[ CAS No. 16635-95-3 ] {[proInfo.proName]}

Name: 16635-95-3|(1R,2R)-rel-1,2-Diphenylethane-1,2-diamine|98%
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Quality Control of [ 16635-95-3 ]

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Product Details of [ 16635-95-3 ]

CAS No. :	16635-95-3	MDL No. :	MFCD00082751
Formula :	C₁₄H₁₆N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	212.29	Pubchem ID :	-
Synonyms :

Safety of [ 16635-95-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 16635-95-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 16635-95-3 ]

[ 16635-95-3 ] Synthesis Path-Downstream 1~17

1
[ 29841-69-8 ]
[ 541-41-3 ]
[ 234753-20-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate In tetrahydrofuran; water at 0 - 20℃; for 4h;
	In ethanol Ambient temperature;
	With pyridine In benzene for 2h;

Reference： [1]Ao, Yu-Fei; Guo, Hao; Meng, Wei; Wang, De-Xian; Wang, Qi-Qiang; Zhang, Lie-Wei; Zhou, Hao [Angewandte Chemie - International Edition, 2020, vol. 59, # 7, p. 2623 - 2627][Angew. Chem., 2020, vol. 132, p. 2645 - 2649,5]
[2]Kanemasa, Shuji; Hayashi, Takeshi; Tanaka, Junji; Yamamoto, Hidetoshi; Sakurai, Tosio [Journal of Organic Chemistry, 1991, vol. 56, # 14, p. 4473 - 4481]
[3]Hu, Kejiang; Krakowiak, Krzysztof E.; Bradshaw, Jerald S.; Dalley, N. Kent; Xue, Guoping; Izatt, Reed M. [Journal of Heterocyclic Chemistry, 1999, vol. 36, # 2, p. 347 - 354]

2
[ 29841-69-8 ]
[ 79-04-9 ]
[ 138051-07-7 ]

Yield	Reaction Conditions	Operation in experiment
89%	With dmap; triethylamine In dichloromethane at 5 - 20℃; for 3h;
70%	With potassium carbonate In chloroform at 20℃; for 3.5h; Cooling with ice;	Synthesis of S-2 (1S, 2S)-1, 2-diphenylethane-1, 2-diamine (1.0 g, 4.7 mmol) wasdissolved in 30 mL of dried chloroform and cooled in the ice bath. 1.4 g (10 mmol) anhydrous K2CO3 was placed in the solution as th ebase. 2-Chloroacetyl chloride (1.6 g, 14.1 mmol) was dropwisely added to the mixture within 30 min. The mixture was then stirred at room temperature for 3 h. After filtration, the filtrate was collected and washed with 20 mL 10% HCl, saturated NaHCO3 and water respectively. The organic layer was dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure.The residue was then purified by column chromatography on silicagel using CHCl3/MeOH (50:1) as eluent to obtain pure products a as a solid (1.20 g, 70%).
843 mg	With dmap; triethylamine In dichloromethane for 3h; Ambient temperature;

Reference： [1]Novacek, Johanna; Roiser, Lukas; Zielke, Katharina; Robiette, Raphaël; Waser, Mario [Chemistry - A European Journal, 2016, vol. 22, # 32, p. 11422 - 11428]
[2]Xu, Kuo-Xi; Kong, Hua-Jie; Zu, Fu-Li; Yang, Li; Wang, Chen-Juan [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 118, p. 811 - 815]
[3]Oi, Ryu; Sharpless, K. Barry [Tetrahedron Letters, 1991, vol. 32, # 37, p. 4853 - 4854]

3
[ 29841-69-8 ]
[ 98-59-9 ]
[ 167316-27-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide; In dichloromethane; at 0 - 5℃; for 3h;Inert atmosphere;	Synthesis of Compound 2009: To a 2-L, three-neck, round-bottom flask equipped with a temperature probe, magnetic stir bar, nitrogen inlet, and addition funnel were added (lS,2S)-(-)-l,2-diphenylethylenediamine (20 g, 0.094 mol) and dichloromethane (160 mL). The mixture was cooled to 0-3 0C and a 1 M solution of sodium hydroxide (160 mL) was added dropwise while maintaining the temperature below 5 0C. To this mixture was added a solution of toluenesulfonyl chloride (17.9 g, 0.094 mol) in dichloromethane (320 mL) dropwise over a 2-h period. The biphasic mixture was stirred at 0-5 0C for an additional 1 h and the reaction was deemed complete by TLC (50% EtO Ac/heptane, UV). Phases were separated and the organic phase was washed with water (2 x 320 mL) and brine (320 mL), dried over sodium sulfate and concentrated to a crude solid. The solid was dissolved in toluene (200 mL) at 70-80 0C and heptane (300 mL) was added portionwise while maintaining this temperature. The resulting slurry was cooled and stirred at 20-25 0C for 1 h and then cooled and stirred at 0-5 0C for 10 min. The solids were filtered and washed with a 50% solution of toluene in heptane (3 x 1 bed volume) to give compound 2009 (30.24 g, 88%) as a white powder.
82.3%	With sodium hydroxide; In dichloromethane; water; at 0 - 20℃; for 3h;	The procedure is the same as in Example 1,Except that (1S, 2S) -1,2-diphenylethylenediamine (3.0 g, 14.1 mmol)Added to 50mLDCM,After stirring and dissolving,A 15 mL aqueous solution of 2N NaOH was added,Cooling to 0 ,A solution of p-toluenesulfonyl chloride (2.65 g, 14.1 mmol)In dichloromethane (30 mL)After maintaining the reaction at 0 C for 1 hour,The temperature was raised to room temperature for 2 hours,HPLC detection reaction ended.The reaction solution was poured into saturated sodium chloride solution (30 mL)Stir for 10 minutes,After stratification,The aqueous phase was extracted once with DCM (30 mL)Combine organic phase,dry,The dichloromethane was removed by distillation under reduced pressure,Get crude.Recrystallization from petroleum ether / ethyl acetate system gave yellow solid Compound I (4.48 g, 82.3%)

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 2505 - 2511
[2]Journal of Organic Chemistry,2004,vol. 69,p. 1283 - 1289
[3]Patent: WO2010/120719,2010,A1 .Location in patent: Page/Page column 194; 196-197
[4]Patent: CN106496099,2017,A .Location in patent: Paragraph 0033; 0034; 0035; 0048; 0049
[5]Organic Syntheses,2005,vol. 82,p. 10 - 17
[6]European Journal of Organic Chemistry,1999,p. 2315 - 2321
[7]Tetrahedron Asymmetry,1997,vol. 8,p. 2101 - 2108
[8]European Journal of Organic Chemistry,2000,p. 2247 - 2252
[9]Patent: EP1174426,2002,A1 .Location in patent: Page 36
[10]Chemistry - A European Journal,2008,vol. 14,p. 7687 - 7698

4
[ 37942-07-7 ]
[ 16635-95-3 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol at 20℃; for 24h;	2.2.1. Synthesis of S,S-DS and R,R-DS (1S,2S)-(-) -1,2-Diphenylethylenediamine (0.2124 g, 1 mmol) was dissolved in 10 mL of absolute ethanol and 2.0 equivalents of 3,5-Bis(tertbutyl)- salicylaldehyde (0.4882 g, 2 mmol) were then added. The color of the reaction mixture turned instantly yellow. After 24 h reaction at room temperature, the powder was filtered and washed by ethanol, and then vacuum dried to obtain pale yellow powders (620 mg, 96%) ( Scheme 1 ). 1 H NMR (400 MHz, CDCl 3 ) 13.58 (s, 1H), 8.39 (s, 1H), 7.31 (d, J = 2.4 Hz, 1H), 6.98 (d, J = 2.4 Hz, 1H), 1.42 (s, 10H), 1.22 (s, 10H) (Fig. S1a) and 13 C NMR (101 MHz, CDCl 3 ) 167.28, 158.00, 140.05, 139.85, 136.43, 128.30, 128.07, 127.43, 127.17, 126.36, 117.91, 80.17, 35.02, 34.06, 31.44, 29.48 (Fig. S1b) can be seen in electronic supplementary in- formation (ESI).
88%	In methanol; dichloromethane at 25 - 30℃;
70%	In ethanol for 3h; Heating;

	In tetrahydrofuran; methanol for 4h; Reflux;
	In tetrahydrofuran; ethanol for 4h; Reflux;
	In ethanol Reflux;

Reference： [1]Tan, Weiqiang; Gao, Jiahui; Guan, Jing; Bi, Xuejun; Tang, Yizhen; Zheng, Chunying; Yan, Tingliang; Zhang, Chenglong [Journal of Molecular Structure, 2022, vol. 1269]
[2]Tak, Rajkumar; Kumar, Manish; Menapara, Tusharkumar; Gupta, Naveen; Kureshy, Rukhsana I.; Khan, Noor-ul H.; Suresh [Advanced Synthesis and Catalysis, 2017, vol. 359, # 22, p. 3990 - 4001]
[3]Pietikäinen, Pekka [Tetrahedron, 2000, vol. 56, # 3, p. 417 - 424]
[4]Yang, Fan; Zhao, Jingnan; Tang, Xiaofei; Zhou, Guangli; Song, Wangze; Meng, Qingwei [Organic Letters, 2017, vol. 19, # 3, p. 448 - 451]
[5]Yang, Fan; Zhao, Jingnan; Tang, Xiaofei; Wu, Yufeng; Yu, Zongyi; Meng, Qingwei [Advanced Synthesis and Catalysis, 2019, vol. 361, # 7, p. 1673 - 1677]
[6]Dadashi-Silab, Sajjad; Stache, Erin E. [Journal of the American Chemical Society, 2022, vol. 144, # 29, p. 13311 - 13318]

5
[ 29841-69-8 ]
[ 18506-04-2 ]
[ 858370-95-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With triethylamine In dichloromethane for 0.166667h; Heating;
97%	Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane; 5-chloro-5H-dibenzo[a,d]cycloheptene In dichloromethane at 20℃; for 2.16667h; Stage #2: With potassium carbonate In dichloromethane; water
97%	In dichloromethane at 20℃; for 2.16667h;	1 Synthesis of (S,S)-1,2-bis(5H-dibenzo[a,d]cyclohepten-5-yl)-1,2-diphenylethanediamine (S,S-DPENtrop2) 667 mg of 5H-dibenzo[a,d]cyclohepten-5-yl chloride (2.95 mmol, 2 eq.) were added at room temperature to 313 mg of (S,S)-diphenylethanediamine (1.47 mmol) in 20 ml of CH2Cl2. After 10 min, a white precipitate formed. The suspension was stirred for a further 2 h and concentrated, and the residue was extracted with 10% by weight aqueous potassium carbonate solution and CH2Cl2. The organic phase was removed and the aqueous phase was extracted twice more with CH2Cl2. The collected organic phases were dried over sodium sulfate and concentrated. Chromatography on silica gel with hexane/diethyl ether (3:2 by volume) and subsequently diethyl ether as eluents gave rise to 846 mg of DPENtrop2 (1.43 mmol, 97%) as a colourless foam. In CDCl3, the compound is present in a symmetrical (approx. 68%) and an asymmetrical (approx. 32%) conformation. Symmetrical form:1H NMR (300 MHz, CDCl3): δ=2.48 (d, J=7.8 Hz, 2H, NH), 3.09 (s, 2H, CHNTrop), 4.49 (d, J=7.8 Hz, 2H, CH(Ph)(NHTrop)), 6.36 (d, J=11.8 Hz, 2H, CHolefin), 6.72 (d, J=11.8 Hz, 2H, CHolefin), 6.83-7.47 (m, 26H, CHaryl). 13C NMR (75 MHz, CDCl3):δ=65.4 (2C, CHNTrop), 66.4 (2C, CH(Ph)(NHTrop)), 126.7 (2C, CHaryl), 126.8 (2C, CHaryl), 126.9 (2C, CHaryl), 127.6 (2C, CHaryl), 128.0 (4C, CHaryl), 128.2 (4C, CHaryl), 128.6 (2C, CHaryl), 129.3 (2C, CHaryl), 129.8 (2C, CHaryl), 129.9 (2C, CHaryl), 130.0 (2C, CHaryl), 130.2 (2C, CHolefin), 130.3 (2C, CHolefin), 133.6 (2C, Cquart), 133.8 (2C, Cquart), 139.3 (2C, Cquart), 140.1 (2C, Cquart), 141.0 (2C, Cquart). IR: v=3317 m, (NH), 3020 m, 1599 w, 1489 m, 1451 s, 1436 s, 1071 m, 797 s, 760 s, 697 s. MS (70 eV, m/z, %): 538 (44), 476 (50), 296 (27), 207 (18), 191 (100). Selected data of asymmetrical form:1H NMR (300 MHz, CDCl3): δ=2.78 (br, 1H, NH), 3.13 (br, 1H, NH), 3.37 (d, J=7.0 Hz, 1H, CH(Ph)(NHTrop)), 3.74 (s, 1H, CHNTrop), 3.74 (d, J=7.0 Hz, 1H, CH(Ph)(NHTrop)), 4.74 (d, J=5.1 Hz, 1H, CHNTrop), 6.82-7.38 (m, 25H, CHaryl ) 7.7 (d, J=7.8 Hz, 1H, CHaryl).

Reference： [1]Maire, Pascal; Breher, Frank; Gruetzmacher, Hansjoerg [Angewandte Chemie - International Edition, 2005, vol. 44, # 39, p. 6325 - 6329]
[2]Current Patent Assignee: LANXESS AG - EP1604973, 2005, A1 Location in patent: Page/Page column 9
[3]Current Patent Assignee: LANXESS AG - US2005/283014, 2005, A1 Location in patent: Page/Page column 5

6
[ 29841-69-8 ]
[ 180740-69-6 ]
[ 1333204-25-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-Bromosuccinimide In dichloromethane at 0 - 20℃;	To a stirred solution of5-(tert-butyl)isophthalaldehyde (660.1 mg, 3.47 mmol) and (1S,2S)-1,2-diphenylethane-1,2-diamine (1.473 g, 6.94 mmol, 2 equiv.) in CH2Cl2 (50 mL),NBS (1.235 g, 6.94 mmol, 2 equiv.) was slowly added at 0 oC. Then, the reaction mixturewas warmed to room temperature and stirred overnight. After the reaction was completed,saturated aqueous NaHCO3 was added, and the mixture was extracted with CH2Cl2. Thecombined organic layer was washed by saturated aqueous brine, dried over Na2SO4, filteredand concentrated in vacuum. The crude product was purified by column chromatography onsilica gel (petroleum ether/EtOAc/Et3N = 6:1:0 to 2:1:0.03) to give the bis(imidazoline)compound A (1.952 g, 98%).
80%	Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane; 5-tert-butylbenzene-1,3-dicarbaldehyde In dichloromethane at 0℃; for 2h; Inert atmosphere; Stage #2: With N-Bromosuccinimide In dichloromethane at 0 - 20℃; Inert atmosphere;	4.3.4. 5-tert-Butyl-bisimidazoline 7 5-(tert-Butyl)isophthalalyde (7d) (50.3 mg, 0.264 mmol) and (S,S)-1,2-diphenyl ethylenediamine (123.3 mg, 0.581 mmol) were dissolved in CH2Cl2 (6 mL) and stirred for 2 h at 0 °C under N2. The resulting solution was added NBS (103.4 mg, 0.581 mmol) at 0 °C and the mixture was stirred overnight at room temperature. The reaction mixture was added to Na2S2O5 aq and 5% NaOH aq, and extracted with CH2Cl2. Organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by SiO2 column chromatography (hexane/AcOEt/triethylamine=2/1/0.03) to give 7 (151.7 mg, 80%) as colorless solid. 1H NMR (400 MHz CDCl3): δ=8.29 (t, J=1.8 Hz, 1H), 8.15 (d, J=1.8 Hz, 2H), 7.39-7.29 (m, 20H), 5.49 (s, 2H), 5.14 (d, J=8.1 Hz, 2H), 4.33 (dd, J=1.8, 8.1 Hz, 2H), 1.42 ppm (s, 9H).

Reference： [1]Li, Nan; Yang, Xiaoyan; Zhu, Yanyan; Wang, Fang; Gong, Junfang; Song, Maoping [Chinese Chemical Letters, 2022, vol. 33, # 5, p. 2437 - 2441]
[2]Location in patent: experimental part Murai, Kenichi; Fukushima, Shunsuke; Nakamura, Akira; Shimura, Masato; Fujioka, Hiromichi [Tetrahedron, 2011, vol. 67, # 26, p. 4862 - 4868]

7
[ 62938-08-3 ]
[ 29841-69-8 ]
[ 1397643-99-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane With potassium carbonate In acetonitrile at 20℃; for 0.5h; Large scale; Stage #2: 3,5-di-tert-butylbenzyl bromide In acetonitrile at 20℃; for 12h; Large scale;	(1) Synthesis of chiral di-secondary amine 3 Add the reaction solvent to the 50L reactor:Acetonitrile (22.0L),Then add chiral ethylenediamine 1 (1.00kg, 4.71mol, 1.00equiv.) andAcid binding agent,The acid binding agent is preferably potassium carbonate (2.00kg, 14.47mol, 3.07equiv.),After stirring for 30 minutes at room temperature,Benzyl bromide 2 (2.81kg, 9.89mol, 2.10equiv.) was slowly added dropwise to the reaction kettle,Then it was stirred at room temperature for 12 hours.After TLC and HPLC are qualified, water (15L) is slowly added to the reaction kettle and stirred at room temperature for 1 hour. The lower aqueous phase was removed by liquid separation, and the upper organic phase was concentrated to obtain a pale yellow solid intermediate 3 (2.91 kg, yield 100%).
83%	With potassium carbonate In acetonitrile at 20℃; for 24h;
80%	With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 20℃; for 24h;

With potassium carbonate In acetonitrile at 20℃;

Reference： [1]Current Patent Assignee: SINO-SINGAPORE INTERNATIONAL JOINT RESEARCH INSTITUTE - CN113185461, 2021, A Location in patent: Paragraph 0032-0033
[2]Zong, Lili; Ban, Xu; Kee, Choon Wee; Tan, Choon-Hong [Angewandte Chemie - International Edition, 2014, vol. 53, # 44, p. 11849 - 11853][Angew. Chem., 2014, vol. 126, # 44, p. 12043 - 12047,5]
[3]Yang, Yuanyong; Moinodeen, Farhana; Chin, Willy; Ma, Ting; Jiang, Zhiyong; Tan, Choon-Hong [Organic Letters, 2012, vol. 14, # 18, p. 4762 - 4765]
[4]Wang, Chao; Zong, Lili; Tan, Choon-Hong [Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10677 - 10682]

8
[ 2052-07-5 ]
[ 29841-69-8 ]
[ 1451929-18-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 10h; Inert atmosphere;
60%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; for 18h; Glovebox;	1 In a glove box, into a 50 mL single-port flask added were 2-phenylbromobenzene 2a (2.33 g, 10.0 mmol), (S,S)-1,2-phenyl-1,2-ethylenediamine 1a (4.24 g, 20.0 mmol, 2.0 equiv), Pd2(dba)3 (230 mg, 0.25 mmol), racemic BINAP (310 mg, 0.5 mmol), sodium tert-butoxide (1.34 g, 14.0 mmol, 1.4 equiv) and 15 mL of toluene, refluxed at 110° C. for 18 h. The mixture was cooled to room temperature, and then added with 20 mL of ethyl acetate for dilution, and washed with 20 mL of water. Then the organic phase was separated, and the aqueous phase was extracted with ethyl acetate for three times (3×20 mL). Then the organic phases were combined, dried with anhydrous sodium sulfate and filtered. The mother liquor was concentrated and separated by column chromatography (petroleum ether/ethyl acetate=10:1) to obtain 2.19 g of a light yellow solid of the compound of formula 3a, with a yield of 60%. Upon detection, the NMR (nuclear magnetic resonance) data of the compound of formula 3a as obtained in this example was: 1H NMR (400 MHz, CDCl3) δ 7.48 (dd, J=14.1, 6.8 Hz, 1H), 7.39 (t, J=8.8 Hz, 1H), 7.28 (d, J=4.0 Hz, 2H), 7.19 (dd, J=12.5, 5.2 Hz, 2H), 7.14 (d, J=7.2 Hz, 1H), 7.01 (d, J=7.2 Hz, 1H), 6.92 (t, J=7.6 Hz, 1H), 6.59 (t, J=7.2 Hz, 1H), 6.20 (d, J=8.0 Hz, 1H), 5.33 (s, 1H), 4.45 (s, 1H), 4.24 (d, J=3.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 144.0, 142.5, 141.2, 139.5, 129.8, 129.5, 129.5, 128.7, 128.5, 128.3, 128.1, 127.6, 127.2, 127.2, 127.1, 126.8, 126.6, 116.2, 111.3, 63.5, 60.7; HRMS (ESI) calcd for C26H24N2 ([M+H]+) 365.2012, found 365.2015.
55%	With 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl; palladium diacetate; sodium butanolate In toluene at 110℃; for 48h; Inert atmosphere; Schlenk technique;

	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 10h; Inert atmosphere;
	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 90℃; for 24h; Inert atmosphere; Glovebox;

Reference： [1]Zhang, Shu-Sheng; Zhao, Yi-Shuang; Tian, Ping; Lin, Guo-Qiang [Synlett, 2013, vol. 24, # 4, p. 437 - 442]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - US2021/253606, 2021, A1 Location in patent: Paragraph 0087-0089
[3]Grassi, David; Dolka, Chrysanthi; Jackowski, Olivier; Alexakis, Alexandre [Chemistry - A European Journal, 2013, vol. 19, # 4, p. 1466 - 1475]
[4]Lu, Hong; Liu, Jin-Yu; Li, Chen-Guang; Lin, Jun-Bing; Liang, Yong-Min; Xu, Peng-Fei [Chemical Communications, 2015, vol. 51, # 21, p. 4473 - 4476]
[5]Ho, Chun-Yu; Chan, Chun-Wa; He, Lisi [Angewandte Chemie - International Edition, 2015, vol. 54, # 15, p. 4512 - 4516][Angew. Chem., 2015, vol. 127, # 15, p. 4595 - 4599,4]

9
[ 29841-69-8 ]
[ 1446100-97-5 ]
[ 1446100-98-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 110℃; for 32h; Inert atmosphere;	4.2.3 Monoaryl diamine 6 At first, NaOtBu (1.56g, 16.4mmol, 3.0equiv) was placed in a 100-mL Schlenk flask and was dried under vacuum at 110°C for 10min. After cooling to room temperature, rac-BINAP (718mg, 1.15mmol, 0.2equiv), Pd(OAc)2 (122mg, 0.54mmol, 0.1equiv), and toluene (47mL) were added and the resulting dark red solution was stirred for 0.5h at room temperature. Bromide 5 (2.00g, 5.42mmol, 1.0equiv) and (1S,2S)-(-)-diphenylethylenediamine (1.73g, 8.15mmol, 1.5equiv) were added to the solution and the mixture was stirred at 110°C for 32h. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2 and the organic layer was washed with water, dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (3:1 to 2:1 hexane/EtOAc) to give 6 as a light yellow solid (2.33g, 86% yield). Title compound 6 exists as a mixture of atropisomers and the ratio (6:4) was determined by 1H NMR analysis. Mp: 73-75°C. 1H NMR (CDCl3): δ 1.32 (br s, 2H), 2.99 (s 1.2H), 3.31 (s, 1.8H), 3.82 (s, 3H), 4.20 (d, J=4.7Hz, 0.4H), 4.25 (d, J=3.6Hz, 0.6H), 4.43 (br s, 0.6H), 4.50 (br s, 0.4H), 5.13 (d, J=5.8Hz, 0.4H), 5.35 (d, J=6.6Hz, 0.6H), 6.19 (d, J=8.0Hz, 0.6 H), 6.30 (d, J=8.3Hz, 0.4 H), 6.61 (q, J=7.2Hz, 1H), 6.93-7.46 (m, 19H). 13C NMR (CDCl3): Due to the complexity of the spectra, signal assignment based on the atropisomerism is difficult and not shown here. δ 55.52, 60.31, 60.76, 61.19, 63.29, 63.82, 110.90, 111.08, 111.49, 115.95, 116.36, 120.32, 120.34, 123.57, 123.61, 124.73, 125.30, 126.92, 127.02, 127.09, 127.14, 128.02-128.74 (m), 130.26 130.54, 131.28, 131.32, 131.53, 131.78, 132.04, 132.22, 132.48, 132.55, 132.97, 141.37, 141.90, 142.59, 142.82, 144.40, 144.47, 156.15, 157.00. HRMS-ESI (m/z): [M+H]+ calcd for C34H33N2O2, 501.25365; found: 501.25302. [α]21D=-41.85[α]D21=-41.85 (c 1.07, CHCl3).

Reference： [1]Iwai, Tomohiro; Akiyama, Yuki; Sawamura, Masaya [Tetrahedron Asymmetry, 2013, vol. 24, # 12, p. 729 - 735]

10
2-chloro-1,3-diisopropyl-4,5-dimethylimidazolium tetrafluoroborate [ No CAS ]
[ 29841-69-8 ]
BF₄^(1-)*C₂₅H₃₅N₄⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium fluoride; triethylamine In chloroform; acetonitrile at 20℃; for 72h; Inert atmosphere; Glovebox; Schlenk technique;	7 2.7. Synthesis and characterization of [DPEN(ImiPrH)NH2][BF4] (6) Acetonitrile (30 mL) was added to a mixture of 3.03 g(10.0 mmol; 1 eq) of 1, 2.45 g (11.5 mmol; 1.15 eq) of (1S,2S)-()-1,2-diphenylethylenediamine and 3.49 g (60.1 mmol; 6 eq) ofKF. To the resulting suspension, 4.2 mL (30 mmol; 3 eq) of NEt3were added. The mixture was stirred at room temperature for3 days to afford a white suspension in a colorless solution. Whilestirring, 30 mL of CHCl3 were added. The mixture was filteredthrough Celite. The Celite filtrate was extracted once with 10 mLof CHCl3. The clear solution was shaken once with a solution of5.5 g (50 mmol) of NaBF4 in 150 mL of water. The organic phasewas then washed once with a dilute NaOH solution (2.3 g in150 mL of water) and once with a dilute NaBF4 solution (5.5 g in150 mL of water). The organic layer was dried over Na2SO4, andthe solvent was then removed in vacuo, affording the product asa pale brown sticky solid (4.47 g, 9.34 mmol, 93%). 1H NMR(400 MHz; CDCl3): d 7.20-7.08 (m, 10H, HAr) 6.21 (bs, 1H, NH),5.00 (sept, 2H, JHH 7.0 Hz, CHMe2), 4.62 (d, 1H, JHH 9.0 Hz, NH2-HCH(Ph)CH), 3.96 (d, 1H, JHH 9.0 Hz, CNHCH(Ph)CH), 2.19 (s, 6H,CCH3), 2.10 (bs, 2H, NH2), 1.54 (d, 6H, JHH 7.0 Hz, CH(CH3)2), 1.03(d, 6H, JHH 7.0 Hz, CH(CH3)2) ppm. 13C NMR (100 MHz; CDCl3): d143.2 (N2CNH), 142.1 (ipso-CAr(CHNH2)), 139.9 (ipso-CAr(CHNH)),128.9 (CAr), 128.4 (CAr), 128.3 (CAr), 127.7 (m-CAr(CHNH2)), 127.5(m-CAr(CHNH), 127.0 (CAr), 123.2 (CMe) 72.5 (CNHCH(Ph)CH),60.2 (NH2HCH(Ph)CH), 49.9 (CHMe2), 21.2 (CH(CH3)2), 20.9(CH(CH3)2), 10.2 (CCH3) ppm. 19F NMR (188 MHz; CDCl3): d152.08 (BF4) ppm. Anal. Calc. for (C25H35BF4N4): C, 62.77; H,7.37; N, 11.71. Found: C, 62.87; H, 7.59; N, 11.22%. ESI-MS:[(M)+]: Calcd.: 391.29; Found: 391.30.

Reference： [1]Volbeda, Jeroen; Jones, Peter G.; Tamm, Matthias [Inorganica Chimica Acta, 2014, vol. 422, p. 158 - 166]

11
[ 29841-69-8 ]
C₉H₁₃ClO₅SSi [ No CAS ]
C₂₃H₂₈N₂O₅SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.5%	With triethylamine In dichloromethane at 0 - 20℃; for 4h;	Synthesis of modifi ed TsDPEN ligand. General procedure: (1R, 2R)- or(1S, 2S)-DPEN (0.318 g, 1.5 mmol) was dissolved in 15mL of CH2Cl2 with 0.3 mL of triethylamine, a solutionof 2-(4-chlorosulfonylphenyl)ethyltrimethoxysilane(0.38 g, 1.12 mmol) in 15 mL CH2Cl2 was then addeddropwise at 0°C in 50 mL fl asks. After the dropping wascompleted, the mixture was slowly warmed to roomtemperature and unceasingly stirred for 4 h, then thesolvent was removed in vacuo. The residue subsequentlyfast passed through a 15 cm silica gel column (eluent:Et3N : CH3OH : CH2Cl2 = 1 : 10 : 100), concentrated,and dried in vacuo to obtain 90.5% yield of modifi edDPEN. 1H NMR (400 MHz, CDCl3): 1.95 (s, 2H), 2.03(s, 1H), 3.56 (s, 9H), 4.32 (d, J = 5.3 Hz, 1H), 4.51 (d,J = 5.3 Hz, 1H), 7.02-7.41 (m, 14H). IR (KBr): 3352,3295, 3170, 3061, 3027, 2942, 2840, 1901, 1690, 1603,1494, 1453, 1411, 1342, 1266, 1192, 1153, 1089, and1014 cm-1.

Reference： [1]Yue, Chuan-Jun; Gu, Li-Ping; Zhuang, Ya-Feng; Liu, Bao-Liang [Russian Journal of Applied Chemistry, 2015, vol. 88, # 7, p. 1207 - 1218][Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.)]

12
[ 93962-39-1 ]
[ 29841-69-8 ]
C₄₀H₅₀N₄O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: (2S,4R)-4-(but-3-en-1-yloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: (S,S)-1,2-diphenyl-1,2-diaminoethane In dichloromethane at 40℃; for 24h;	2 Embodiment 2 Compound3 (0.97g, 3 . 60mmol) dissolved in dichloromethane (10 ml), 0 °C stirring, add triethylamine (0.81 ml, 5 . 85mmol) and ethyl chloroformate (0.36 ml, 3 . 82mmol), maintaining 0 °C stirring 30 min, then adding (1S, 2S)-bisphenylmethyl ethylenediamin (0.47g, 2 . 25mmol), 40 °C reaction 24h. After the reaction, solution concentration, column chromatography (methanol/dichloromethane = 1/45, volume ratio), vacuum drying to obtain white solid4a (1.03g, 80%).

Reference： [1]Current Patent Assignee: HUBEI UNIVERSITY - CN105330687, 2016, A Location in patent: Paragraph 0015

13
[ 29841-69-8 ]
[ 57190-17-7 ]
(1S,2S)-1,2-diphenyl-N₁,N₂-bis(2,6-diisopropylphenyl)ethane-1,2-diamine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 9317 - 9324

14
[ 21524-34-5 ]
[ 29841-69-8 ]
(1S,2S)-1,2-diphenyl-N₁,N₂-bis(2,4,6-triisopropylphenyl)ethane-1,2-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-3-imidazolium chloride; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate at 115℃; for 20h; Inert atmosphere; Glovebox; Sealed tube;
70%	With bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In toluene at 110℃; for 24h; Inert atmosphere;	2.1 (1) Synthesis of diamine compound 2b: Add 5mmol of (1S,2S)-(-)-1,2-diphenylethylenediamine, 18mmol of tBuONa, 15mmol of 2,4,6-triisopropyl bromobenzene, 1.5mmol of IPrMe·HCl, Mix 0.5 mmol of Pd(dba)2, add 20 mL of anhydrous toluene, and react at 110°C for 24 hours under a nitrogen atmosphere. After the reaction is completed, it is diluted with water, extracted with ethyl acetate 3 times, and dried with anhydrous Na2SO4. The solvent was spin-dried under reduced pressure, and the crude product was subjected to silica gel column chromatography to obtain a white solid (eluent: petroleum ether/dichloromethane = 10:1). Product yield: 2.15 g, yield: 70%.

Reference： [1]Wang, Hengbin; Lu, Gang; Sormunen, Grant J.; Malik, Hasnain A.; Liu, Peng; Montgomery, John [Journal of the American Chemical Society, 2017, vol. 139, # 27, p. 9317 - 9324]
[2]Current Patent Assignee: SUN YAT-SEN UNIVERSITY (CHINA) - CN112209972, 2021, A Location in patent: Paragraph 0093; 0096-0097

15
[ 29841-69-8 ]
[ 132939-08-3 ]
C₄₂H₄₀N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane; 2-Hydroxy-2'-methoxy-<1,1'-biphenyl>-3-carboxaldehyde With acetic acid In ethanol Inert atmosphere; Molecular sieve; Reflux; Stage #2: With sodium tetrahydroborate at 0 - 20℃;	1 Preparation of ligand L3 (R is 2-methoxyphenyl) (1S,2S)-1,2-diphenylethylenediamine (1.0 mmol, 212 mg, 1.0 equiv) was dissolved in 50 mL of absolute ethanol under argon. Then 3-(2-methoxy)phenyl salicylaldehyde (2.0 mmol, 456 mg, 2.0 equiv) was added. Stirring was continued for 10 min, then 5 drops of acetic acid, molecular sieves were added in sequence. The reaction solution was refluxed overnight to react. The temperature was lowered to 0 ° C, and NaBH 4 (3.0 mmol, 113 mg, 3.0 equi) was added portionwise and stirred at room temperature overnight. After the reaction is completed, the resulting mixed solution is evaporated to dryness. The resulting solid is then quenched with NH4Cl.Stir for 30 min and extract 3 times with CH2Cl2. Washed twice with saturated brine, dried over anhydrous NaSO4, The solvent was evaporated to dryness, recrystallized from ethanol to give L3 (541mg, 0.85mmol, 85% yield).
	Multi-step reaction with 2 steps 1: ethanol / 10 h / Inert atmosphere; Schlenk technique; Reflux 2: sodium tetrahydroborate / ethanol / 3 h / 20 °C / Inert atmosphere; Schlenk technique; Cooling with ice

Reference： [1]Current Patent Assignee: UNIVERSITY OF JINAN (SHANDONG) - CN109776338, 2019, A Location in patent: Paragraph 0027-0033
[2]Chen, Jie; Gu, Haiyang; Zhu, Xueying; Nam, Wonwoo; Wang, Bin [Advanced Synthesis and Catalysis, 2020, vol. 362, # 14, p. 2976 - 2983]

16
[ 29841-69-8 ]
[ 75462-59-8 ]
C₃₂H₂₄F₁₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: (S,S)-1,2-diphenyl-1,2-diaminoethane With potassium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: 3,5-bis(trifluoromethyl)benzyl chloride With tetrabutylammomium bromide In acetonitrile at 20℃; for 12h;	1 (1) Synthesis of chiral bis-secondary amine 3 Add the reaction solvent: acetonitrile (3.50L) to the 10L reaction kettle, then add chiral diphenylethylenediamine 1 (150.00g, 0.70mol, 1.00equiv.) and acid binding agent in sequence,The acid binding agent is preferably potassium carbonate (289.80 g, 1.58 mol, 3.00 equiv.).After stirring for 30 minutes at room temperature,Benzyl chloride 2 (397.90 g, 1.47 mol, 2.10 equiv.) was added dropwise to the reaction kettle, and then TBAB (23.32 g, 0.07 mol, 0.10 equiv.) was added and then stirred at room temperature for 12 hours. After TLC and HPLC were qualified, water (2.0L) was slowly added to the reaction kettle and stirred at room temperature for 1 hour. The lower aqueous phase was removed by liquid separation, and the upper organic phase was concentrated to obtain a pale yellow solid: chiral di-secondary amine 3 (471.60 g, yield 100%), which can be used directly in the next reaction without further purification.

Reference： [1]Current Patent Assignee: SINO-SINGAPORE INTERNATIONAL JOINT RESEARCH INSTITUTE - CN113185500, 2021, A Location in patent: Paragraph 0029-0031

17
[ 29841-69-8 ]
[Ir(PyBz)₂Cl]₂ [ No CAS ]
C₁₁₄H₈₄Ir₂N₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With toluene-4-sulfonic acid In toluene; acetonitrile at 120℃; for 10h; Inert atmosphere;	3 Example 3 Synthesis of target compound LP4: Λ-fac-Ir-CHO (37.0 mg, 0.05 mmol) and(1S,2S)-1,2-diphenylethylenediamine (25.4 mg, 0.12 mmol)placed in a 50 mL three-necked flask,To this was added 45 mL of toluene and acetonitrile solvent with a volume ratio of 1:2.5,Stir to dissolve completely,Then add 15 mol% p-toluenesulfonic acid,The reaction was carried out under argon atmosphere at 120 °C for 10 h.After the reaction solution was cooled to room temperature,Under reduced pressure distillation to obtain orange-yellow solid,It was dissolved in dichloromethane and diffused with ether to give crystalline LP4, 46.5 mg, yield 93%.

Reference： [1]Current Patent Assignee: UNIV DALIAN TECH - CN114213465, 2022, A Location in patent: Paragraph 0025

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