(3'R)-1'-(Phenylmethyl)-1,3'-bipyrrolidine → (3R)-3-(Pyrrolidin-1-YL)pyrrolidine

HRID 1641899Notes

Reaction equation

HRID 1641899 reaction equation
C([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[N:13]1([C@@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 66629680(3'R)-1'-(Phenylmethyl)-1,3'-bipyrrolidine

Product 1

HCID 7176272(3R)-3-(Pyrrolidin-1-YL)pyrrolidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of (R)-1′-benzyl-[1,3′]bipyrrolidinyl (0.517 g, 2.24 mmol) in methanol (25 ml) under an atmosphere of argon is treated with palladium hydroxide on carbon (0.1 g). The reaction mixture is placed under an atmosphere of hydrogen, stirred at room temperature overnight and then filtered through Celite™ filter material. The filtrate is concentrated in vacuo to yield the title compound as a dark orange oil.

Workup

  1. filtrationfiltered through Celite™
  2. filtrationfilter material
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-6a9e0c8e1b69458293c4bc6d6043da63
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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