Potassium Carbonate → methyl 4-[(2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinyl]methoxybenzoate

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Reaction Steps

To a stirred solution of methyl 4-[(2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinyl]methoxybenzoate (7.43 g, 18.9 mmol) in MeOH (150 ml) was added cat. K2CO3 at room temperature. After 1 day stirring, the mixture was concentrated in vacuo. The resulting residue was recrystallized by the addition of CHCl3-n-hexane, to give methyl 4-[(2S,4S)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinyl]methoxybenzoate (5.76 g, 87%) as a colorless solid. 1H-NMR (CDCl3) δ 1.46 (s, 9H), 2.11 (m, 1H), 2.35 (br, 1H), 3.27–3.65 (m, 2H), 3.89 (s, 3H), 4.07–4.54 (m, 4H), 6.96 (d, J=6.9 Hz, 2H), 7.99 (d, J=6.9 Hz, 2H).

Provenance & Evidence