Sodium cyanoborohydride → HCID 69221574, compound

Participants

Reaction Steps

To a stirred slurry of tert-butyl (1S)-1-formyl-2-methyl-2-phenylpropyl(methyl) carbamate (104 mg, 0.40 mmole, Reference Example 19) with ethyl 4-[(2-Amino-3,3-dimethyl-butyryl)-methyl-amino]-2,5-dimethyl-hex-2-enoic acid ethyl ester (122 mg, 0.40 mmole) in MeOH (2.5 ml), a solution of zinc chloride (32.7 mg, 0.6 eq) and sodium cyanoborohydride (34.4 mg, 0.48 mmol) in MeOH (2.5 ml) is added over 5 minutes at room temperature. The resulting mixture is stirred for 15-24 hours at room temperature under an inert atmosphere. After concentration, the residue is taken up in ethylacetate, washed with sodium bicarbonate. The aqueous phase is extracted with ethylacetate. The combined organic layers is washed with brine, dried and is chromatographed (silica gel, flash column) to give a white solid. (0.164 mg, 81%) M.W. 587.8 [M+H] 588.3

Provenance & Evidence