Acetone → HCID 52913246, compound

Participants

Reaction Steps

A cooled (−20° C.) solution of 0.29 g (0.50 mmol) of (S)-2-[(S)-4-(3-Chloro-4-trifluoromethyl-phenylcarbamoyl)-3-methyl-2-oxo-piperazin-1-yl]-5-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-5-oxo-pentanoic acid methyl ester in 1.5 ml of THF was treated with 0.25 ml (0.50 mmol) of LiBH4 (2 M in THF) and 0.04 ml (1.00 mmol) of MeOH in 0.3 ml of THF. The reaction was warmed to +15° C. (during 3 h) and stirred for 1.5 h at RT, cooled to 0° C. and stopped with 0.17 ml (2.28 mmol) of acetone. The reaction was partitioned between aqueous 10% KHSO4/EtOAc (3×). The organic phases were washed with aqueous saturated NaHCO3, aqueous 10% NaCl, dried (Na2SO4) and evaporated to give after flash silica gel column (dichloromethane/MeOH 96:4 to 95:5) and precipitation (dichloromethane/ether) 0.19 g (68%) of the title compound as white amorphous powder. MS: 561.21 (MH+, Cl).

Provenance & Evidence