Acetone → 3-[(3-Chloro-4-trifluoromethoxy-phenyl)-(2-hydroxy-ethyl)-amino]-propionic acid tert-butyl ester

Participants

Reaction Steps

A solution of 3.00 g (7.3 mmol) of 3-[(3-chloro-4-trifluoromethoxy-phenyl)-methoxycarbonylmethyl-amino]-propionic acid tert-butyl ester in 20 ml of THF was treated with 4.44 ml (8.9 mmol) of LiBH4 (2 M in THF) and 0.59 ml (14.6 mmol) of MeOH (with cooling bath at RT). The reaction was stirred for 2 h at RT, cooled to 0° C. and stopped with 2 ml of acetone. The reaction was diluted with 4.5 ml of cyclohexane, 18 ml of aqueous 2 N NaOH were added and after 30 min extracted with EtOAc (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated to give after flash silica gel column (EtOAc:n-heptane 1:4 to 1:1) 2.21 g (78%) of the titled compound as light yellow oil. MS: 384.12 (MH+, Cl).

Provenance & Evidence