(s)-3-Fluoropyrrolidine hydrochloride → 4-[(3S)-3-fluoro-1-pyrrolidinyl]-1-[3-(methyloxy)-4-nitrophenyl]piperidine

Participants

Reaction Steps

1-[3-(methyloxy)-4-nitrophenyl]-4-piperidinone (1.0 g, 4.0 mmol) and (S)-(+)-3-fluoropyrrolidine hydrochloride were subjected to reductive amination analogous to the procedure for 3,3-difluoro-1′-[3-(methyloxy)-4-nitrophenyl]-1,4′-bipiperidine (Intermediate B41) to give 4-[(3S)-3-fluoro-1-pyrrolidinyl]-1-[3-(methyloxy)-4-nitrophenyl]piperidine in quantitative yield. 1H NMR (400 MHz, d6-DMSO) δ 7.84 (d, J=9.6 Hz, 1H), 6.56 (dd, J=9.4 and 2.2 Hz, 1H), 6.47 (d, J=2.0 Hz, 1H), 5.24-5.07 (m, 1H), 3.91-3.87 (m, 5H), 3.05-2.99 (m, 2H), 2.88-2.77 (m, 2H), 2.70-2.58 (m, 1H), 2.38-2.26 (m, 2H), 2.14-1.98 (m,1H), 1.88-1.75 (m, 3H), 1.46-1.36 (m, 2H).

Provenance & Evidence