317336-73-5|tert-Butyl 2,3,6,7-tetrahydro-1H-azepine-1-carboxylate| Ambeed

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Quality Control of [ 317336-73-5 ] Purity: 98% SDS Specification

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Product Details of [ 317336-73-5 ]

CAS No. :	317336-73-5
Formula :	C₁₁H₁₉NO₂
M.W :	197.27
SMILES Code :	CC(C)(C)OC(=O)N1CCC=CCC1
MDL No. :	MFCD10688298
InChI Key :	XUNAYZIHVQJKGX-UHFFFAOYSA-N
Pubchem ID :	12969195

Safety of [ 317336-73-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 317336-73-5 ]

* 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.

Upstream synthesis route of [ 317336-73-5 ]
Downstream synthetic route of [ 317336-73-5 ]

[ 317336-73-5 ] Synthesis Path-Upstream 1~9

1
[ 1211531-07-5 ]
[ 317336-73-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Grubbs catalyst first generation In dichloromethane at 45℃; for 2 h;	A 1 L round-bottomed flask equipped with a reflux condenser was charged with 500 mL of dichloromethane (DCM), followed by addition of tert-butyl di(but-3-en-1- yl)carbamate (1.00 g, 4.44 mmol), prepared according to the method of Kuhn, K. M. et al., Organic Letters 2010 12 (5), 984-987. The solution was heated up to 45°C. Grubbs 1 generation catalyst (238 mg, 0289 mmol) was added. The reaction mixture was allowed to reflux at 45°C for 2 hours. The solvent was removed with a rotary evaporator. Purification by column chromatography with 4percent ethyl acetate in hexanes yielded 790 mg (4.01 mmol, 9Qpercent) of the title compound as an oil.

References: [1] Organic Letters, 2010, vol. 12, # 5, p. 984 - 987.
[2] Patent: WO2016/164565, 2016, A1, . Location in patent: Page/Page column 9.
[3] Journal of Medicinal Chemistry, 2019, .

2
[ 317336-90-6 ]
[ 317336-73-5 ]

References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371.

3
[ 793-19-1 ]
[ 317336-73-5 ]

References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371.

4
[ 5279-23-2 ]
[ 317336-73-5 ]

References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371.

5
[ 14002-33-6 ]
[ 317336-73-5 ]

References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371.

6
[ 125763-80-6 ]
[ 317336-73-5 ]

References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371.

7
[ 125763-74-8 ]
[ 317336-73-5 ]

References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371.

8
[ 317336-62-2 ]
[ 317336-73-5 ]

References: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371.

9
[ 18940-41-5 ]
[ 317336-73-5 ]

References: [1] Journal of Medicinal Chemistry, 2019, .

[ 317336-73-5 ] Synthesis Path-Downstream 1~31

1
[ 317336-90-6 ]
[ 317336-73-5 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8367 - 8371.

2
[ 317336-73-5 ]
tert-butyl 8-oxa-4-azabicyclo[5.1.0]octane-4-carboxylate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 4293 - 4301.

3
bis-(3-bromo-propyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
[ 317336-73-5 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8367 - 8371.

4
[ 14002-33-6 ]
[ 317336-73-5 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8367 - 8371.

5
[ 793-19-1 ]
[ 317336-73-5 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8367 - 8371.

6
[ 5279-23-2 ]
[ 317336-73-5 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8367 - 8371.

7
[ 125763-80-6 ]
[ 317336-73-5 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8367 - 8371.

8
[ 125763-74-8 ]
[ 317336-73-5 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8367 - 8371.

9
[ 317336-62-2 ]
[ 317336-73-5 ]

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 8367 - 8371.

10
[ 317336-73-5 ]
[ 796062-15-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -60 - 20℃;	To a stirred solution of 16.4 g <strong>[317336-73-5]2,3,6,7-tetrahydro-azepine-1-carboxylic acid tert-butyl ester</strong> in 420 ml dichloromethane was added at -60 C. 35.8 g m-chloroperbenzoic acid (70% purity). The mixture was allowed to slowly warm to room temperature overnight, 1 l ethylacetate was added and the solution was extracted with aqueous sodium bicarbonate, 1N aqueous sodium hydroxide and brine. Evaporation of the solvent and chromatography yielded 14.5 g (82%) 8-oxa-4-aza-bicyclo[5.1.0]octane-4-carboxylic acid tert-butyl ester as colorless liquid; MS (EI): m/e=213 (M+,5%), 158 (22%), 140 (12%), 57 (100%). To a solution of 14.3 g 8-oxa-4-aza-bicyclo[5.1.0]octane-4-carboxylic acid tert-butyl ester in 750 ethanol was added 150 ml water, 35.8 g ammonium chloride and 43.6 g sodium azide. The mixture was stirred at 75 C. over night, the solvents were greatly removed by distillation under vacuum and the residue was suspended in ethanol and filtered. The ethanol was distilled off and the residue was suspended in ethylacetate and filtered. Removal of the solvent and chromatography on silicagel with ethylacetate/hexane 1:1, yielded 13.5 g (79%) 4-azido-5-hydroxy-azepane-1-carboxylic acid tert-butyl ester as a viscous oil; MS (ISP): m/e=257 (M+H+).

References: [1]Patent: US2004/229862,2004,A1 .Location in patent: Page 14, 23.
[2]Patent: WO2017/107979,2017,A1 .Location in patent: Paragraph 1428.

11
[ 1211531-07-5 ]
[ 317336-73-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Grubbs catalyst first generation; In dichloromethane; at 45℃; for 2.0h;	A 1 L round-bottomed flask equipped with a reflux condenser was charged with 500 mL of dichloromethane (DCM), followed by addition of tert-butyl di(but-3-en-1- yl)carbamate (1.00 g, 4.44 mmol), prepared according to the method of Kuhn, K. M. et al., Organic Letters 2010 12 (5), 984-987. The solution was heated up to 45C. Grubbs 1 generation catalyst (238 mg, 0289 mmol) was added. The reaction mixture was allowed to reflux at 45C for 2 hours. The solvent was removed with a rotary evaporator. Purification by column chromatography with 4% ethyl acetate in hexanes yielded 790 mg (4.01 mmol, 9Q%) of the title compound as an oil.

References: [1]Organic Letters,2010,vol. 12,p. 984 - 987.
[2]Patent: WO2016/164565,2016,A1 .Location in patent: Page/Page column 9.
[3]Journal of Medicinal Chemistry,2019.

12
silver nitrate [ No CAS ]
[ 317336-73-5 ]
(4E)-tert-buty-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate.AgNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With benzoic acid methyl ester; In diethyl ether; hexane; at -40 - 0℃; for 3.0h;	The cis-cycloheptene derivative and methyl benzoate (1.43 g, 10.4 mmol, 2.0 equiv)were dissolved in 500 mL of solvent in a round-bottomed flask. The round-bottomedflask was immersed in a cooling bath (NESLAB CB 80 with a CRYCTROL controller, bath temperature was set to -40 C) and connected via PTFE tubing successively to an FMI ?Q? pump, a three-way tee that was equipped with a thermometer probe, a coil of FEP tubing (total length: lm; ID: 1/16 inch; CD 1/8 inch) and a 25g Biotage column asillustrated in FIG. 1. The FEP tubing coil was placed in a Rayonet RPR-100 reactor. The bottom of the column was packed with dry silica gel (6 cm), and the top of the column was packed with silver nitrate impregnated silica (10 wt% of AgNO3, 11.5 g, 1.30 equiv). The column was flushed with 200 mL of the reaction solvent. The pump was turned on and the rate of circulation was adjusted to approx. 100 mL per minute.The temperature at the three-way tee was maintained at 0C. The lamp was then turned on, and photoisomerization of the stirring mixture was carried out for the indicated time. Afterwards, the sensitizer was flushed from the column with 400 mL of 2O% ether in hexanes. The column was then dried by a stream of compressed air, and then flushed with ethanol. The trans-cycloheptene silver (I) complex was collected andstored in a freezer as a solution in ethanol (200 mL).The general photoisomerization procedure was followed by using (4Z)-tert-Butyl2,3,6,7-tetrahydro-1H-azepine-1-carboxylate (133 mg, 0.675 mmol) and 2:3ether:hexanes as solvent. The flow-photoisomerization reaction was carried out for 3hours to provide 119 mg (48% yield) of the title compound in ethanol solution.

References: [1]Patent: WO2016/164565,2016,A1 .Location in patent: Page/Page column 19.

13
[ 317336-73-5 ]
(4R,5S)-4-hydroxy-5-((S)-5H-imidazo[5,1-a]isoindol-5-yl)azepane-1-sulfonamide [ No CAS ]
(4S,5R)-4-hydroxy-5-((R)-5H-imidazo[5,1-a]isoindol-5-yl)azepane-1-sulfonamide [ No CAS ]
(4R,5S)-4-hydroxy-5-((R)-5H-imidazo[5,1-a]isoindol-5-yl)azepane-1-sulfonamide [ No CAS ]
(4S,5R)-4-hydroxy-5-((S)-5H-imidazo[5,1-a]isoindol-5-yl)azeyane-1-sulfonamide [ No CAS ]

References: [1]Patent: WO2017/107979,2017,A1 .

14
[ 317336-73-5 ]
(4R,5S)-5-((S)-5H-imidazo[5,1-a]isoindol-5-yl)-1-(methylsulfonyl)azepan-4-ol [ No CAS ]
(4S ,5R)-5-((R)-5H-imidazo[5,1-a]isoindol-5-yl)-1-(methylsulfonyl)azepan-4-ol [ No CAS ]
(4R,5S)-5-((R)-5H-imidazo[5,1-a]isoindol-5-yl)-1-(methylsulfonyl)azepan-4-ol [ No CAS ]
(4S,5R)-5-((S)-5H-imidazo[5,1-a]isoindol-5-yl)-1-(methylsulfonyl)azepan-4-ol [ No CAS ]

References: [1]Patent: WO2017/107979,2017,A1 .

15
[ 317336-73-5 ]
tert-butyl 4-hydroxy-5-(5H-imidazo[5,1-a]isoindol-5-yl)azepane-1-carboxylate [ No CAS ]

References: [1]Patent: WO2017/107979,2017,A1 .

16
[ 317336-73-5 ]
5-(5H-imidazo[5,1-a]isoindol-5-yl)azepan-4-ol [ No CAS ]

References: [1]Patent: WO2017/107979,2017,A1 .

17
[ 317336-73-5 ]
tert-butyl ((4-hydroxy-5-(5H-imidazo[5,1-a]isoindol-5-yl)azepan-1-yl)sulfonyl)carbamate [ No CAS ]

References: [1]Patent: WO2017/107979,2017,A1 .

18
[ 317336-73-5 ]
[ 1263282-12-7 ]