3-Methylbutanal → cis-2-(3-Methylbutylamino)-cyclopentanecarboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

(1R,2S)-2-Amino-cyclopentanecarboxylic acid ethyl ester hydrochloride (0.81 g, 4.18 mmol) was dissolved in methanol (40 mL). Sodium acetate (0.69 g, 8.36 mmol) was added followed by 4 Å powdered molecular sieve (0.81 g). Isovaleraldehyde (0.36 g, 4.18 mmol) was then added followed by sodium cyanoborohydride (0.6 g, 10.45 mmol). The reaction mixture stirred at 25° C. for 16 h. The mixture was poured into saturated aqueous sodium bicarbonate solution (150 mL). The aqueous layer was extracted with ethyl acetate (2×150 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to afford the crude product, (1R,2S)-2-(3-methyl-butylamino)-cyclopentanecarboxylic acid ethyl ester (0.58 g, 2.55 mmol, 61%), as a clear oil. LC-MS (ESI) calcd for C13H25NO2 227.19, found 228.2 [M+H+].

Provenance & Evidence