Methyl valinate hydrochloride → Methyl (2S)-2-(hept-6-en-1-ylamino)-3-methylbutanoate

Participants

Reaction Steps

To a solution (0.3M) of L-valine, methyl ester, hydrochloride in dry MeOH was added ZnCl2 (1.0 eq.), NaCNBH3 (1.2 eq.), hept-6-enal 66 (1.2 eq.), and the reaction mixture was stirred at RT overnight. Then the volatiles were evaporated at reduced pressure and the residue taken-up in CH2Cl2 and washed with a saturated aq. solution of NaHCO3. The organic layer was dried over Na2SO4 and evaporated at reduced pressure affording the title compound (98%) as yellow pale oil.

Provenance & Evidence