Sodium borohydride → 2-(5-[(1S)-1-benzyloxycarbonylamino-ethyl]-3-benzyl-2-hydroxy-cyclohept-4-en-1-yl)-1-oxo-ethyl-valinyl-valine methyl ester

Participants

Reaction Steps

To a stirred solution of the above (38) (0.47 g) in ethanol (15 mL) was added at room temperature NaBH4 (55 mg). After stirring for 30 min the reaction was carefully quenched with acetone then aqueous 1N HCl. The reaction was extracted with ethyl acetate, washed with saturated NaCl, dried over MgSO4 and evaporated. The product (39) was obtained as a mixture of isomers by flash chromatography on silica gel eluted with 50% CHCl3 in ethyl acetate (0.42 g, 89%). TLC Rf 0.36, 0.33 (97:3 CHCl3 :MeOH); MS DCl/NH3 (M+H)+ =650.4.

Provenance & Evidence