(R)-((S)-1-phenylethyl)2-(2-fluorophenyl)-2-(piperidin-1-yl)acetate → (R)-2-(2-fluorophenyl)-2-(piperidin-1-yl)acetic acid

HRID 68266Notes

Reaction equation

HRID 68266 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:9]([O:11][C@H](C1C=CC=CC=1)C)=[O:10]>C(O)C.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:8]([N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 1

HCID 59166523(R)-((S)-1-phenylethyl)2-(2-fluorophenyl)-2-(piperidin-1-yl)acetate

Product 1

HCID 27326965(R)-2-(2-fluorophenyl)-2-(piperidin-1-yl)acetic acidYield 98.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

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)+.

Workup

  1. customwas hydrogenated at room temperature
  2. customThe solution was then purged with Ar
  3. filtrationfiltered through diatomaceous earth (Celite®)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19fa3d8941e646e9973213d6bd16f2a8
Source dataset
uspto-grants-2014_09
Patent number
US08822444B2

Reaction notes

Loading…