Potassium Hydroxide → 4-[(tert-Butoxycarbonyl)amino]-4-(carboxymethyl)tetrahydro-2H-pyran, 4-Amino-4-(carboxymethyl)tetrahydro-2H-pyran, N-BOC protected

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(4-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-4-yl)acetate (0.73 g, 2.67 mmol) in ethanol (5 mL) and water (2 mL) was added potassium hydroxide (0.3 g, 5.34 mmol) at room temperature. Upon completion of addition, the reaction mixture was heated at 60° C. for 4 hours and then partitioned between ethyl acetate (30 mL) and 1N HCl (10 mL). The ethyl acetate layer was separated, washed with brine (20 mL), dried over sodium sulfate and concentrated to yield the title compound (0.615 g) as a white solid. MS found: (M−H)+=258.2.

Provenance & Evidence