Ammonia → ((3R,4S)-4-Phenylpyrrolidin-3-YL)methanol

HRID 1182166Notes

Reaction equation

HRID 1182166 reaction equation
C([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:10]([CH2:19][OH:20])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].N>C(O)C.CO.[OH-].[Pd+2].[OH-]>[C:13]1([C@H:11]2[CH2:12][NH:8][CH2:9][C@@H:10]2[CH2:19][OH:20])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 222AmmoniaHCID 2723923Ammonium formateHCID 21341047((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol

Product 1

HCID 20638814((3R,4S)-4-Phenylpyrrolidin-3-YL)methanolYield 82.6%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To ((3R,4S)-1-benzyl-4-phenyl-pyrrolidin-3-yl)-methanol (2.28 g, 8.54 mmol) in ethanol (200 mL) was added ammonium formate (5.39 g, 85.49 mmol) and palladium hydroxide (446 mg, 20 wt % Pd) and the mixture was refluxed for 1.5h. Ammonia in methanol (0.8 mL, 2M) was added to the reaction mixture and refluxed for an additional 0.5h. The reaction mixture was filtered through celite and concentrated to give ((3R,4S)-4-phenyl-pyrrolidin-3-yl)-methanol as a colorless oil (1.25 g) which was used directly in the next step.

Workup

  1. temperaturethe mixture was refluxed for 1.5h
  2. temperaturerefluxed for an additional 0.5h
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1989dd61df5045aeaf49f236badc7430
Source dataset
uspto-grants-2007_10
Patent number
US07288548B2

Reaction notes

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