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.
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Doi:10.1016/j.ejmech.2020.113023
(2021)Doi:10.1016/0040-4039(95)01509-G
(1995)Doi:10.1007/BF00476785
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(1993)Doi:10.1016/S0040-4039(00)84352-X
(1986)Doi:10.1016/0304-5102(93)85084-7
(1993)
