113486-06-9|tert-Butyl (2-methylbut-3-yn-2-yl)carbamate| Ambeed

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Quality Control of [ 113486-06-9 ] Purity: 95% SDS Specification

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Product Details of [ 113486-06-9 ]

CAS No. :	113486-06-9
Formula :	C₁₀H₁₇NO₂
M.W :	183.25
SMILES Code :	O=C(OC(C)(C)C)NC(C#C)(C)C
MDL No. :	MFCD16036595
InChI Key :	RXPXPDDPWDNBGV-UHFFFAOYSA-N
Pubchem ID :	10655060

Safety of [ 113486-06-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335-H303
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 113486-06-9 ]

* 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 [ 113486-06-9 ]

[ 113486-06-9 ] Synthesis Path-Downstream 1~35

1
[ 16330-13-5 ]
[ 113486-06-9 ]
[ 113486-09-2 ]

References: [1]Tetrahedron,1987,vol. 43,p. 2721 - 2732.

2
[ 24424-99-5 ]
[ 2978-58-7 ]
[ 113486-06-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	In dichloromethane; at 20℃; for 15h;	Example 3; N-(2-dH-l,2,3-triazol-4-yl')propan-2-ylV4-r3.,4-dichlorophenoxy')piτ)eridine- 1 -sulfonamide[0094] Step A: Preparation of tert-butyl 2-methylbut-3-yn-2-ylcarbamate: A solution of dimethylpropargylamine (3.0 g, 36 mmol) and Boc anhydride (7.5 g, 34 mmol) in DCM (73 rnL) was stirred at room temperature for 15 hours. The reaction mixture was washed with dilute aqueous HCl, and the organic layer was dried with MgSO4 and concentrated in vacuo to afford tert-butyl 2-methylbut-3-yn-2-ylcarbamate (6.0 g, 91%) as a solid. 1H NMR (400 MHz. CDCl3) δ 2.30 (s, IH), 1.55 (s, 3H)5 1.53 (s, 3H)5 1.46 (s5 9H).
91%	In dichloromethane; at 20℃; for 15h;	Example 4 JV-(2-('lH-l,2,3-triazol-5-yl)propan-2-vD-4-('5-cvanopyridin-2-yl)piperazine-l-sulfonamide; [0097] Step A: Tert-butyl 2-methylbut-3-yn-2-ylcarbamate: A solution of dimethylpropargylamine (3.0 g, 36 mmol) and Boc anhydride (7.5 g, 34 mmol) in DCM (73 mL) was stirred at room temperature for 15 hours. The reaction mixture was washed with dilute aqueous HCl5 and the organic layer was dried with MgSO4. The organic layer was concentrated in vacuo to afford tert-butyl 2-methylbut-3-yn-2-ylcarbamate (6.0 g, 91%) as a white solid. 1H NMR (400 MHz. CDCl3) δ 2.30 (s, IH), 1.55 (s, 3H), 1.53 (s, 3H), 1.46 (s, 9H).
82%	at 50℃; for 0.5h;	A mixture of 1 ,1 -dimethylpropargylamine (4.2g) and B0C2O (1 1 g) without solvent was warmed up to 50C for 30 min. The resulting solid was treated with n-hexane (10 mL) and the product was collected by filtration to give white solid (7.6 g, yield 82%)

35.6%	at 50℃; for 0.5h;	A mixture of 2-methyl-3-butyn-2-amine (1 mL) and di-tert-butyl dicarbonate (2.07 g) without solvent was warmed up to 50 CC for 30 mm. The resulting solution was diluted with nhexane (5 mL) and the crystals formed were, subsequently, collected by filtration, washed with hexane and dried under vacuum to give 620 mg of the title compound (yield: 35.6%).
35.6%	at 50℃; for 0.5h;	A mixture of 2-methyl-3-butyn-2-amine (1 mL) and di-tert-butyl dicarbonate (2.07 g) without solvent was warmed up to 50 C for 30 min. The resulting solution was diluted with n- hexane (5 mL) and the crystals formed were, subsequently, collected by filtration, washed with hexane and dried under vacuum to give 620 mg of the title compound (yield: 35.6%).

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2731 - 2734.
[2]Patent: WO2008/147764,2008,A1 .Location in patent: Page/Page column 21.
[3]Patent: WO2008/147763,2008,A1 .Location in patent: Page/Page column 21.
[4]Patent: WO2013/169401,2013,A1 .Location in patent: Page/Page column 70.
[5]Tetrahedron,1987,vol. 43,p. 2721 - 2732.
[6]Chemistry - An Asian Journal,2019,vol. 14,p. 4352 - 4357.
[7]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 631 - 638.
[8]Patent: WO2017/153459,2017,A1 .Location in patent: Page/Page column 31.
[9]Patent: WO2019/43103,2019,A1 .Location in patent: Page/Page column 31-32.
[10]Organic Letters,2015,vol. 17,p. 520 - 523.
[11]Journal of the American Chemical Society,2021,vol. 143,p. 12622 - 12632.

3
[ 113486-06-9 ]
[ 154181-80-3 ]
[ 154181-91-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 631 - 638.

4
[ 113486-06-9 ]
4,4-dimethyl-5-methyleneoxazolidin-2-one [ No CAS ]

References: [1]Synlett,2006,p. 2727 - 2730.
[2]Synlett,2008,p. 1399 - 1401.

5
[ 2930-05-4 ]
[ 113486-06-9 ]
{1-[1-(3-benzyloxy-2-hydroxypropyl)-1H-[1,2,3]triazol-4-yl]-1-methylethyl}-carbamic acid t-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium azide; at 80℃; for 10h;Green chemistry;	General procedure: An equimolar mixture of epoxides 1 and NaN3 wasstirred for 10 min in 1 g of IL i.e. [bmim]Br, loaded withCu(I) at 5 mol% w.r.t. reactant concentration. To theresultant, were added an equimolar ratio of terminalalkynes 2 via a syringe and the reaction was furthermaintained under stirring at 80 8C for a specified period oftime. After completion of the reaction (as indicated byTLC), 10 mL of distilled water were added under continuousstirring, and solid crude product obtained was simplycollected by filtration. Purification of crude products wascarried out by recrystallization from ethanol. The filtratecontaining IL and the Cu(I) catalyst was immediatelyreduced under low pressure and further dried at 100 8C for20-30 min in a hot air oven, for the consecutive reactionruns. Physical data of some representative compounds aregiven below.

References: [1]Comptes Rendus Chimie,2015,vol. 18,p. 1257 - 1263.
[2]Journal of Organic Chemistry,2007,vol. 72,p. 9822 - 9825.

6
[ 113486-06-9 ]
7-(3-Amino-3-methyl-but-1-ynyl)-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1998,vol. 46,p. 631 - 638.

7
[ 113486-06-9 ]
[ 113486-14-9 ]

References: [1]Tetrahedron,1987,vol. 43,p. 2721 - 2732.

8
[ 113486-06-9 ]
[ 113486-17-2 ]

References: [1]Tetrahedron,1987,vol. 43,p. 2721 - 2732.

9
[ 109608-77-7 ]
[ 113486-06-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dimethyl 1-(1-diazo-2-oxopropyl)phosphonate; potassium carbonate; In methanol; at 0 - 10℃; for 6h;	To a solution of dimethyl 1-diazo-2-oxopropyl phosphonate (see Ohira, S. Synth. Commun. 19, 561-564, (1989) ) (2.97 g, 15.5 mmol) in methanol (50 ml) at 0 C was added potassium carbonate (1.71g, 12.4 mmol) and slowly a solution OFN-BOC-2-AMINO-2-METHYL- propionaldehyde (1.45 g, 7.74 mmol) in methanol (5 ml). The reaction mixture was stirred at 0-10 C for additional 6 h, diluted with diethylether (-150 ml) and with saturated aqueous ammonium chloride solution (150 ml). The organic layer was washed with saturated aqueous ammonium chloride solution (100 ml), water (100 ml), and finally with brine, dried over sodium sulfate, and concentrated in vacuo. Purification by flash chromatography over silica gel using ethyl acetate/hexane (1/10) provided N-BOC-2-AMINO-2-METHYLBUT-3-YNE (1.38 g) as yellowish oil.

References: [1]Patent: WO2005/19174,2005,A1 .Location in patent: Page/Page column 52-53.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 552A tert-butyl 1,1-dimethylprop-2-ynylcarbamate The desired product was prepared by substituting 1,1-dimethyl-prop-2-ynylamine for propargylamine in Example 516A. 1H NMR (300 MHz, DMSO-D6) δ ppm 1.39 (s, 9H), 1.42 (s, 6H), 3.02 (s, 1H), 6.94 (s, 1H).

11
[ 113486-06-9 ]
[ 1088886-63-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With trimethylsilylazide;copper(l) iodide; In methanol; N,N-dimethyl-formamide; at 100℃; for 15h;	Step B: Preparation of tert-butyl 2-(3H-l52,3-triazol-4-yl)propan-2- ylcarbamate: In a 150 mL pressure vessel, tert-butyl 2-methylbut-3-yn-2-ylcarbamate (6.00 g5 32.7 mmol) was dissolved in 9:1 DMF/MeOH (65 mL). CuI (0.312 g, 1.64 mmol) and azidotrimethylsilane (5.22 mL, 39.3 mmol) were added. After heating to a temperature of 1000C for 15 hours, the reaction mixture was concentrated in vacuo and the residue diluted in DCM. After extracting with IN NaOH (3 times), the aqueous layer was neutralized with 2N HCl and extracted with DCM (3X). The combined organic layers were dried with MgSO4 and concentrated in vacuo to afford tert-butyl 2-(3H-l,2,3-triazol-4-yl)propan-2-ylcarbamate (5.49g, 74%) as a solid. MS APCI (+) m/z 226.8 detected. 1H NMR (400 MHz. CDCl3) δ 7.56 (s, IH), 5.10 (br s, IH), 1.70 (s, 6H), 1.41 (s, 9H).
74%	With trimethylsilylazide;copper(l) iodide; In methanol; N,N-dimethyl-formamide; at 100℃; for 15h;	Step B: Tert-butyl 2-(3H-l,2,3-triazol-4-yl)propan-2-ylcarbamate: In a 150 mL pressure vessel, tert-butyl 2-methylbut-3-yn-2-ylcarbarnate (6.00 g, 32.7 mmol) was dissolved in 9:1 DMF/methanol (65 mL). CuI (0.312 g, 1.64 mmol) and azidotrimethylsilane <n="23"/>("TMSN3", 5.22 mL, 39.3 mmol) were added to this solution. After heating the solution to a temperature of 1000C for 15 hours, the reaction mixture was concentrated in vacuo, and the residue was diluted in DCM. After extracting with IN NaOH (3X), the aqueous layer was neutralized with 2N HCl (aq) and extracted with DCM (3X). The combined organic layers were dried with MgSO4 and concentrated in vacuo to afford tert-butyl 2-(3H-l,2,3-triazol-4- yl)propan-2-ylcarbamate (5.49g, 74%) as a solid. MS APCI (+) m/z 226.8 detected. 1H NMR (400 MHz. CDCl3) δ 7.56 (s, IH), 5.10 (br s, IH), 1.70 (s, 6H), 1.41 (s, 9H).

References: [1]Patent: WO2008/147764,2008,A1 .Location in patent: Page/Page column 21.
[2]Patent: WO2008/147763,2008,A1 .Location in patent: Page/Page column 21-22.

12
[ 637-81-0 ]
[ 113486-06-9 ]
C₁₄H₂₄N₄O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2731 - 2734.

13
[ 1226913-43-4 ]
[ 113486-06-9 ]
[ 1163298-03-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2731 - 2734.

14
[ 1120-87-2 ]
[ 113486-06-9 ]
C₁₅H₂₀N₂O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2731 - 2734.

15
[ 113486-06-9 ]
N-(2-(3-amino-3-methylbut-1-yn-1-yl)-5-((5-chloro-4-((2-(dimethylphosphoryl)phenyl)amino)pyrimidin-2-yl)amino)-4-methoxyphenyl)acrylamide [ No CAS ]

References: [1]Patent: WO2013/169401,2013,A1 .

16
[ 113486-06-9 ]
C₂₉H₃₆ClN₆O₄P [ No CAS ]

References: [1]Patent: WO2013/169401,2013,A1 .

17
[ 113486-06-9 ]
C₃₂H₃₈ClN₆O₅P [ No CAS ]

References: [1]Patent: WO2013/169401,2013,A1 .

18
C₁₉H₁₈BrClN₅O₄P [ No CAS ]
[ 113486-06-9 ]
C₂₉H₃₄ClN₆O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 4h;	To a mixture of compound A (527 mg) and step-1 product (250 mg) in DMF (5.0 mL), was added (Ph3P)2PdCl2 (0.1 g), Cul (0.05 g) and Et3N (0.2 mL). The mixture was stirred at 80C for 4h. The reaction mixture was concentrated and the residue was purified by a prep-TLC plate (8%MeOH/DCM) to give final product as a yellow solid (430 mg, yield 68%).

References: [1]Patent: WO2013/169401,2013,A1 .Location in patent: Page/Page column 70-71.

19
[ 4202-14-6 ]
[ 109608-77-7 ]
[ 113486-06-9 ]

References: [1]Journal of Organic Chemistry,2014,vol. 79,p. 1254 - 1264.

20
[ 113486-06-9 ]
[ 33244-86-9 ]

References: [1]Journal of Organic Chemistry,2014,vol. 79,p. 1254 - 1264.

21
[ 113486-06-9 ]
[ 1542244-60-9 ]

References: [1]Journal of Organic Chemistry,2014,vol. 79,p. 1254 - 1264.

22
[ 113486-06-9 ]
3-amino-3-methylbutanoic acid hydrochloride [ No CAS ]

References: [1]Journal of Organic Chemistry,2014,vol. 79,p. 1254 - 1264.

23
[ 113486-06-9 ]
[ 2978-58-7 ]

References: [1]Journal of Organic Chemistry,2014,vol. 79,p. 1254 - 1264.

24
[ 24424-99-5 ]
[ 113486-06-9 ]
3-methyl-3-[bis(tert-butoxycarbonyl)amino]but-1-yn [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 520 - 523.

25
[ 113486-06-9 ]
4-methyl-4-[bis(tert-butoxycarbonyl)amino]pent-2-yn-1-ol [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 520 - 523.

26
[ 113486-06-9 ]
(E)-4-methyl-4-[bis(tert-butoxycarbonyl)amino]-2-(tributylstannyl)pent-2-en-1-ol [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 520 - 523.

27
[ 113486-06-9 ]
C₁₅H₁₇NO₂ [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 520 - 523.

28
[ 113486-06-9 ]
C₂₀H₂₅NO₄ [ No CAS ]

References: [1]Organic Letters,2015,vol. 17,p. 520 - 523.

29
[ 113486-06-9 ]
C₁₂H₁₄N₆ [ No CAS ]