(S)-4-[(E)-2-(6-chloro-pyridin-3-yl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → (S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Participants

Reaction Steps

To a stirred suspension of (S)-4-[(E)-2-(6-chloro-pyridin-3-yl)-vinyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.0 g) in methanol (70 ml) was added platinum on charcoal (0.58 g, 10 wt %) and the mixture was stirred under an atmosphere of hydrogen at room temperature for 15 min. The mixture was then filtered through celite and the filtrate was concentrated in vacuo to give (S)-4-[2-(6-chloro-pyridin-3-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (949 mg, 94%) as a colourless oil. MS (ISP): 343.2 ([{37Cl}M+H]+), 341.1 ([{35Cl}M+H]+), 287.0 ([{37Cl}M+H—C4H8]+), 285.1 ([{35Cl}M+H—C4H8]+).

Provenance & Evidence