(R)-((S)-1-phenylethyl) 2-(dimethylamino)-2-(2-fluorophenyl)acetate TFA salt → (R)-2-(Dimethylamino)-2-(2-fluorophenyl)acetic acid

HRID 1809291Notes

Reaction equation

HRID 1809291 reaction equation
OC(C(F)(F)F)=O.[CH3:8][N:9]([CH3:29])[C@H:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])[C:11]([O:13][C@H](C1C=CC=CC=1)C)=[O:12]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:8][N:9]([CH3:29])[C@H:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[F:28])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 86659243(R)-((S)-1-phenylethyl) 2-(dimethylamino)-2-(2-fluorophenyl)acetate TFA salt

Product 1

HCID 26722549(R)-2-(Dimethylamino)-2-(2-fluorophenyl)acetic acidYield 98%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of (R)—((S)-1-phenylethyl) 2-(dimethylamino)-2-(2-fluorophenyl)acetate TFA salt (1.25 g, 3.01 mmol) and 20% Pd(OH)2/C (0.125 g) in ethanol (30 mL) was hydrogenated at room temperature and atmospheric pressure (H2 balloon) for 4 hours. The solution was then purged with Ar, filtered through diatomaceous earth (CELITE®), and concentrated in vacuo. This gave the title compound as a colorless solid (0.503 g, 98%). 1H NMR (400 MHz, CD3OD) δ 7.53-7.63 (m, 2H), 7.33-7.38 (m, 2H), 5.36 (s, 1H), 2.86 (s, 6H). LC-MS: Anal. Calcd. for C10H12FNO2: 197; found: 198 (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-e94b998066684f94a812c6465ca0f2e7
Source dataset
uspto-grants-2013_01
Patent number
US08362020B2

Reaction notes

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