Reacción #1772026

ord-d58874139736422db73733131c6c2f16

Ecuación de reacción

C[C@H](OC(=O)[C@@H](c1ccccc1F)N1CCCCC1)c1ccccc1
(R)-((S)-1-phenylethyl) 2-(2-fluorophenyl)-2-(piperidin-1-yl)acetate
O=C(O)[C@@H](c1ccccc1F)N1CCCCC1
title compound
Rendimiento 98.1%
O=C(O)[C@@H](c1ccccc1F)N1CCCCC1
(R)-2-(2-fluorophenyl)-2-(piperidin-1-yl)acetic acid
Rendimiento 98.1%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrowas hydrogenated at room temperature
  2. 2
    OtroThe solution was then purged with Ar
  3. 3
    Filtraciónfiltered through diatomaceous earth (Celite®)
  4. 4
    Concentraciónconcentrated in vacuo

Procedimiento

A mixture of (R)-((S)-1-phenylethyl) 2-(2-fluorophenyl)-2-(piperidin-1-yl)acetate (0.737 g, 2.16 mmol) and 20% Pd(OH)2/C (0.070 g) in ethanol (30 mL) was hydrogenated at room temperature and atmospheric pressure (H2 balloon) for 2 hours. The solution was then purged with Ar, filtered through diatomaceous earth (Celite®), and concentrated in vacuo. This provided the title compound as a colorless solid (0.503 g, 98%). 1H NMR (400 MHz, CD3OD) δ 7.65 (ddd, J=9.1, 7.6, 1.5 Hz, 1H), 7.47-7.53 (m, 1H), 7.21-7.30 (m, 2H), 3.07-3.13 (m, 4H), 1.84 (br s, 4H), 1.62 (br s, 2H). LCMS: Anal. Calcd. for C13H16FNO2: 237. found: 238 (M+H)+.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08147818B2uspto-grants-2012_04