1-Naphthaleneethanamine → HCID 11733389, compound

Participants

Reaction Steps

(2S,4S)-2-Formyl-4-BOCsulfanyl-pyrrolidine-1-carboxylic acid allyl ester (1) (1.84 g) in dichloromethane(20 ml) was added dropwise over 10 minutes to a mixture of 2-naphthalen-1-ylethylamine (1.0 g),. sodium triacetoxyborohydride(1.36 g) and 4A powdered molecular sieve (3.0 g) in dichloromethane (130 ml) cooled to −20° C. and stirred under an argon atmosphere. After the addition was complete the reaction was allowed to warm to ambient temperature and stirred for a further 18 hours. The molecular sieves were filtered off and the fitrate stirred with saturated aqueous sodium bicarbonate solution( 100 ml) for 5 minutes. The mixture was separated, the organic phase dried over magnesium sulphate and applied to a silica flash column which was then eluted with 1.Ethyl acetate/Hexane(50:50), 2.Ethyl acetate/Hexane(80/20), 3.Ethyl acetate to give (2S,4S)-4-BOCsulfanyl-2[(2-naphthalen-1-ylethylamino)-methyl]pyrrolidine-1-carboxylic acid allyl ester (2) (2.2 g) as a colourless gum.

Provenance & Evidence