Trifluoroacetic acid → Methyl 4-(4,4-difluoro-2-pyrrolidinylmethoxy)benzoate

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Reaction Steps

A mixture of methyl 4-[1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethoxy]benzoate (830 mg, 2.23 mmol) and TFA (5 ml) in CH2Cl2 (5 ml) was stirred for 3 h and concntrated in vacuo. The residue was made basic with sat. NaHCO3 and extracted with CHCl3 (2×200 ml). The combined extracts were dried over K2CO3 and concntrated in vacuo to give methyl 4-(4,4-difluoro-2-pyrrolidinylmethoxy)benzoate (550 mg, 91%) as a pale yellow solid. 1H-NMR (CDCl3) δ 2.19 (m, 1 H), 2.43 (m, 1 H), 3.19–3.41 (m, 2 H), 3.77 (m, 1 H), 3.89 (s, 3 H), 4.00–4.09 (m, 2 H), 6.92 (d, J=9.0 Hz, 2 H), 7.99 (d, J=9.0 Hz, 2 H); MS (FAB) m/z 272 (M++1); Anal. Calcd for C13H15F2NO3: C, 57.56; H, 5.57; N, 5.16. Found: C, 57.65; H, 5.67; N, 5.16.

Provenance & Evidence