Chemical and Pharmaceutical Bulletin p. 1128 - 1131 (1996)
Update date:2022-09-26
Topics: Analog Pyrrolidine Preparation Experimental terms L-aspartic acid Amino
Yoshida, Toshihiko
Takeshita, Makoto
Orita, Hitomi
Kado, Noriyuki
Yasuda, Shingo
Kato, Hideo
Itoh, Yasuo
(3S,4S)-3-(tert-Butoxycarbonyl)amino-4-methylpyrrolidine (12a) was synthesized from L-aspartic acid (4) on a large scale. Methylation of dimethyl (2S)-N-benzyl-N-(9-phenylfluoren-9-yl)aspartate (5), easily derived from 4, with methyl iodide gave (3R)-3-methylaspartate (6a) in 91% yield with high diastereoselectivity. Reduction of 6a with lithium aluminum hydride, followed by hydrogenolysis, protection with di-tert-butyl dicarbonate, and mesylation gave 10a in 89% overall yield. Subsequently, reaction of 10a with benzylamine under a nitrogen atmosphere at room temperature, followed by hydrogenolysis, gave the target compound (12a) in 65% overall yield. In a similar manner to that described for the preparation of 12a from 5, compound 5 was converted into 4-ethyl and 4-propyl derivatives (12b,c) in 34% and 38% overall yields.
View MoreZhonghao (dalian) Research and Design Institute of Chemical Industry Co., Ltd
Contact:+86 411 84674606
Address:201, Huangpu Road , Shahekou District, Dalian ,116023-China
Jiangsu Cale New Material Co.ltd
Contact:+86-515-88334667/88203550
Address:Zhongshan 3rd Road, Coastal Chemical Industry Park, Yancheng, Jiangsu, China
Shanghai birch chemical technology co.,ltd
Contact:+86-21-54096810
Address:No.2588,Jungong Road,Shanghai,China
Beijing Harmony Chemical Co., Ltd.
Contact:86-010-84956928
Address:Room 207, Jin feng he B building, No 8 Xin Jie Kou Wai Street, Xi Cheng District, Beijing,PRC. 10008
Chengdu Boon Stream Chemical Industry Co.,Ltd.
Contact:+86-28-83156758
Address:No.859,Dongzikou Road,Jinniu District,Chengdu,Sichuan,P.R.China
Doi:10.1016/j.ejmech.2020.113023
(2021)Doi:10.1016/0040-4039(95)01509-G
(1995)Doi:10.1007/BF00476785
()Doi:10.1016/S0040-4039(00)60310-6
(1993)Doi:10.1016/S0040-4039(00)84352-X
(1986)Doi:10.1016/0304-5102(93)85084-7
(1993)