(2S,3'S)-2-Methyl-1'-(6-nitro-pyridin-3-yl)-[1,3']bipyrrolidinyl → HCID 68211102, compound

HRID 2401105Notes

Reaction equation

HRID 2401105 reaction equation
[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@H:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[N:14][C:15]([N+:18]([O-])=O)=[CH:16][CH:17]=2)[CH2:8]1>CO.[Pd]>[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C@H:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[N:14][CH:13]=2)[CH2:8]1

Participants

4

Reactant 1

HCID 68213028(2S,3'S)-2-Methyl-1'-(6-nitro-pyridin-3-yl)-[1,3']bipyrrolidinyl

Product 1

HCID 68211102HCID 68211102, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2S,3′S)-2-methyl-1′-(6-nitro-pyridin-3-yl)-[1,3′]bipyrrolidinyl (0.11 g, 0.398 mmol) in methanol (30 mL) in a 250 mL parr bottle was added 5% Pd/C (0.03 g). The reaction mixture was allowed to shake under a hydrogen atmosphere (55 psi) at room temperature for 3 hours. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated under vacuum to afford 0.091 g (93%) of title compound.

Workup

  1. customat room temperature
  2. customfor 3 hours
  3. filtrationThe reaction mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-2daee542ec244728912fb8cf1566fa45
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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