Acetone → (S)-4-[(S)-4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-4-oxo-butyl]-2-methyl-3-oxo-piperazine-1-carboxylic acid (3-chloro-4-trifluoromethoxy-phenyl)-amide

Participants

Reaction Steps

A solution of 0.200 g (0.34 mmol) of (S)-2-[(S)-4-(3-chloro-4-trifluoromethoxy-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 (example 54) in 1.0 ml of THF was treated with 0.17 ml (0.34 mmol) of LiBH4 (2 M in THF) and 0.027 ml (0.68 mmol) of MeOH (with cooling bath at RT). The reaction was stirred for 2 h at RT, cooled to 0° C. and stopped with 0.1 ml of acetone. The reaction was diluted with 0.3 ml of cyclohexane, 0.9 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 (dichloromethane/MeOH 98:2 to 9:1) 0.172 g (88%) of the titled compound as white foam. MS: 577.20 (MH+, Cl).

Provenance & Evidence