(R)-4-(3-Fluoropyrrolidin-1-yl)-1-(3-methoxy-4-nitrophenyl)piperidine → 4-{4-[(3R)-3-fluoro-1-pyrrolidinyl]-1-piperidinyl}-2-(methyloxy)aniline

Participants

Reaction Steps

4-[(3R)-3-fluoro-1-pyrrolidinyl]-1-[3-(methyloxy)-4-nitrophenyl]piperidine (1.33 g, 4.0 mmol) was reduced in a manner analogous to 4-(3,3-difluoro-1,4′-bipiperidin-1′-yl)-2-(methyloxy)aniline (Intermediate B38) above. The filtrate was washed with water, dried over magnesium sulfate and concentrated to give 4-{4-[(3R)-3-fluoro-1-pyrrolidinyl]-1-piperidinyl}-2-(methyloxy)aniline (1.01 g, 86% yield). 1H NMR (400 MHz, d6-DMSO) δ 6.48-6.45 (m, 2H), 6.26 (dd, J=8.4 and 2.4 Hz, 1H), 5.24-5.07 (m, 1H), 4.16 (s, 2H), 3.70 (s, 3H), 3.33-3.30 (m, 2H), 2.88-2.76 (m, 2H), 2.69-2.56 (m,1H), 2.54-2.46 (m under DMSO peak, 2H), 2.37-2.31 (m, 1H), 2.14-1.99 (m, 2H), 1.90-1.75 (m, 3H), 1.51-1.41 (m, 2H).

Provenance & Evidence