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

HRID 657714Notes

Reaction equation

HRID 657714 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 refluxed for 1.5 h. Ammonia in methanol (0.8 mL, 2M) was added to the reaction mixture and refluxed for an additional 0.5 h. 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. temperaturerefluxed for 1.5 h
  2. temperaturerefluxed for an additional 0.5 h
  3. filtrationThe reaction mixture was filtered through celite and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f305e9aadcc94217b2b0aa3e02b80b34
Source dataset
uspto-grants-2011_12
Patent number
US08076349B2

Reaction notes

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