Dimethylamine → N-[(1R)-3-(Dimethylamino)-1-(hydroxymethyl)-3-oxopropyl]carbamic acid phenylmethyl ester

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Reaction Steps

A solution of 3-(S)-((carbobenzyloxy)amino)-γ-butyrolactone (prepared according to the procedure described in McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952, 7.72 g, 32.8 mmol) in THF (100 mL) was saturated with gaseous dimethylamine, stirred at room temperature for 16 hours, and concentrated. The residue was filtered through a plug of silica gel eluting with 50% acetone in hexanes to give the desired product (9.16 g, 99%). MS (CI) m/e 281 (M+H)+.

Provenance & Evidence