Sodium triacetoxyborohydride → (4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-methyl-4-((R)-1-phenylethylimino)-tetrahydro-2H-pyran-3-carboxylate (crude, 13.53 mmol) in acetonitrile-acetic acid (1:1, 80 mL) was treated with NaBH(OAc)3 and stirred for 2.5 h at 0° C. Following concentration in vacuo, the residue was dissolved in ethyl acetate (200 mL), washed with saturated NaHCO3 until the aqueous phase was basic, dried over MgSO4, and purified by chromatography with 20% ethyl acetate/hexane to yield 1.37 g (37% in 2 steps) of (4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate. MS: (M+H)+=278.1.

Provenance & Evidence