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ChemicalBook CAS DataBase List (3S)-3-AMinoazepane-1-carboxylic Acid tert-Butyl Ester
625471-04-7

(3S)-3-AMinoazepane-1-carboxylic Acid tert-Butyl Ester synthesis

2synthesis methods
BOC-OSU

13139-12-3

(R)-3-Amino-Hexahydro-1H-Azepin

107885-67-6

(3S)-3-AMinoazepane-1-carboxylic Acid tert-Butyl Ester

625471-04-7

The general procedure for the synthesis of tert-butyl (S)-3-aminoazepane-1-carboxylate from tert-butyl N-succinimidocarbonate and (S)-azepan-3-amine was as follows: (S)-azepan-3-ylamine (5 g, 43.8 mmol) was dissolved in 100 mL of anhydrous dichloromethane and cooled to -78 °C with magnetic stirring. In another flask, N-tert-butoxycarbonyloxy sulfonamidine (Boc-OSu, 9.7 g, 45 mmol) was dissolved in 50 mL of anhydrous dichloromethane. The succinimide solution was slowly added to the stirring amine solution over 10-15 minutes, keeping the reaction mixture at -78 °C. After addition, the reaction mixture was allowed to gradually warm to room temperature and stirring was continued for 4 hours or the completion of the reaction was confirmed by thin layer chromatography (TLC, ninhydrin color development; Rf 0.3; unfolding reagent ratio of 0.1:1:10 ammonia, methanol and dichloromethane). The reaction mixture was washed with 50 mL of water, and the aqueous layer was adjusted to pH >13 by addition of 6N sodium hydroxide and subsequently extracted with dichloromethane (3 × 100 mL). The organic layer was dried over anhydrous sodium carbonate, filtered and concentrated in vacuum to give pure tert-butyl (S)-3-aminoazepane-1-carboxylate as a viscous oil (5.1 g, 54% yield).

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Yield:625471-04-7 54%

Reaction Conditions:

in dichloromethane at -78 - 20; for 4.16667 - 4.25 h;

Steps:

26
Example 26 2-R (AMINOCARBONYL) AMINOL-N-R (3S)-AZEPAN-3-VLL-5-(4-METHOXD7PHENVL) THIOPHENE-3 carboxamide hydrochloride (S)-3-AMINO-AZEPANE-1-CARBOXYLIC acid tert-butyl ester. (S)-Azepan-3-ylamine (5g ; 43.8 mmol) was dissolved in 100 mL of anhydrous CH2C12 and cooled to-78 °C while stirring with a magnetic stirring bar. In another flask N-(TERT-BUTOXYCARBONYLOXY) SUCCINIMIDE [BOC-OSU] (9.7 g; 45 mmol) was dissolved in 50 ML of anhydrous CH2C12. To the stirred solution of the amine was added the solution of the SUCCINIMIDE over a period of 10-15 minutes so as to keep the reaction mixture at-78 °C while stirring. After the addition was complete, the reaction was allowed to warm to room temperature and then stirred for an additional 4h or until the reaction was complete by TLC (Ninhydrin; Rf 0.3 ; 0.1 : 1: 10 NH4OH, MeOH ; CH2C12). The reaction mixture was washed with 50 mL of H20. The aqueous layer was brought to a pH >13 by the addition of 6N NAOH and extracted with CH2C12 (3 x 100 mL). The organic layer was dried over Na2C03, filtered, and concentracted in a vacuum to yield pure (S)-3-AMINO-AZEPANE-L-CARBOXYLIC acid tert- butyl ester as a viscous oil (5.1 g, 54%).

References:

ASTRAZENECA AB;ASTRAZENECA UK LIMITED WO2005/16909, 2005, A1 Location in patent:Page/Page column 68

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