HCID 57803411, compound → HCID 57803415, compound

HRID 2367031Notes

Reaction equation

HRID 2367031 reaction equation
C([O:8][C@H:9]1[CH2:13][N:12]([C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C@H:11]([CH:30]([CH3:32])[CH3:31])[CH2:10]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[OH:8][C@H:9]1[CH2:13][N:12]([C:14](=[O:29])[CH2:15][NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:27])[F:25])[CH:19]=2)[C@H:11]([CH:30]([CH3:32])[CH3:31])[CH2:10]1

Participants

4

Reactant 1

HCID 57803411HCID 57803411, compound

Product 1

HCID 57803415HCID 57803415, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

N-{2-[(2S,4R)-4-Benzyloxy-2-isopropylpyrrolidin-1-yl]-2-oxoethyl}-3-(trifluoromethyl)benzamide (0.630 g, 1.40 mmol) was dissolved in methanol (60 mL) and then palladium hydroxide (90 mg) was added to the solution. The flask was purged with hydrogen and then stirred under an atmosphere of hydrogen using a balloon. After three hours, TLC indicated complete consumption of starting material. The reaction was then flushed with nitrogen and filtered through Celite on a glass frit and washed with methanol. The filtrate was concentrated to give the desired alcohol as a white solid, 0.52 g (100%). LC/MS (M+H)+ m/z=359.2; 1H NMR (CDCl3) δ 8.11 (m, 2H), 7.53-7.82 (m, 3H), 4.04-4.52 (m, 4H), 3.63 (m, 1H), 3.43 (m, 1H), 2.50 (m, 1H), 1.86-2.25 (m, 2H), 0.89 (d, 3H), 0.78 (d, 3H).

Workup

  1. customThe flask was purged with hydrogen
  2. customconsumption of starting material
  3. customThe reaction was then flushed with nitrogen
  4. filtrationfiltered through Celite on a glass frit
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8e7ab6198d03474a9f7cd3b9d2178e89
Source dataset
uspto-grants-2014_04
Patent number
US08697870B2

Reaction notes

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