1-Naphthalenemethanamine → HCID 86756699, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (2S,4S)-2-formyl-4-BOCsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (compound (1)) (3.11 grm. ) in dichloromethane(60 ml.) was added dropwise to a stirred mixture of of 1-naphthalenemethylamine (1.71 g), 4A molecular sieves(12 grms) and sodium triacetoxyborohydride(2.3 grms) in dichloromethane (200 ml) under an argon atmosphere at −20°. The mixture was stirred for a further 30 minutes at −20° C. and then allowed to warm to ambient temperature and stirred for a further 16 hours. The mixture was filtered and washed with aqueous sodium bicarbonate solution (2×200 ml),the organic phase further washed with water (200 ml), separated, dried over magnesium sulphate and purified by column chromatography, using ethyl acetate/hexane (30:70) as eluent to give (2S,4S)-2-{[naphthalen-1-ylmethyl]-amino)-methyl}-4-BOCsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (compound(12)) as a pale yellow oil (2.09 g).

Provenance & Evidence