Water → Carbamic acid, [1-(methoxymethyl)cyclopentyl]-, phenylmethyl ester

Participants

Reaction Conditions

Reaction Steps

To a cold solution (0° C.) of (1-hydroxymethyl-cyclopentyl)-carbamic acid benzyl ester (250 mg, 1 mmol) and 48% aqueous HBF4 (0.13 ml, 1 mmol) in CH2Cl2 (4 mL) was added TMSCHN2 (2N in hexane, 2 mL, 4 mmol) via syringe. The resulting mixture was stirred, at 0° C., for ½ hour followed by the addition of water (10 mL). The aqueous mixture was extracted with CH2Cl2 (2×50 mL), and the combined organic layers were dried (sodium sulfate), filtered, concentrated and chromatographed with 30% ethyl acetate/hexane to provide the titled compound. MS (DCI) m/e 264 (M+H)+.

Provenance & Evidence