(2S,3'S)-2-Methyl-1'-(6-methyl-5-nitro-pyridin-2-yl)-[1,3']bipyrrolidinyl → 2-Methyl-6-((2S,3'S)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl-amine

HRID 536308Notes

Reaction equation

HRID 536308 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:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([CH3:21])[N:13]=2)[CH2:8]1>CO.[Pd]>[CH3:21][C:14]1[C:15]([NH2:18])=[CH:16][CH:17]=[C:12]([N:9]2[CH2:10][CH2:11][C@H:7]([N:3]3[CH2:4][CH2:5][CH2:6][C@@H:2]3[CH3:1])[CH2:8]2)[N:13]=1

Participants

4

Reactant 1

HCID 71280938(2S,3'S)-2-Methyl-1'-(6-methyl-5-nitro-pyridin-2-yl)-[1,3']bipyrrolidinyl

Product 1

HCID 674803792-Methyl-6-((2S,3'S)-2-methyl-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl-amineYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2S,3′S)-2-methyl-1′-(6-methyl-5-nitro-pyridin-2-yl)-[1,3′]bipyrrolidinyl (0.633 g, 2.18 mmol) in methanol (60 mL) in a 250 mL parr shaker bottle was added 5% Pd/C (0.200 g). The reaction mixture was allowed to shake under a hydrogen atmosphere (55 psi) at room temperature for 4 hours. The reaction mixture was filtered through a pad of Celite and the filtrate was concentrated under vacuum to afford 0.544 g (96%) of title compound.

Workup

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

Sources & evidence

ORD record
ord-33484874ff774f08883d2f43f078635a
Source dataset
uspto-grants-2014_10
Patent number
US08859588B2

Reaction notes

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