2-((S)-3-Methoxy-pyrrolidin-1-ylmethyl)-5-nitro-pyridine → HCID 90359314, compound

HRID 55877Notes

Reaction equation

HRID 55877 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=2)[CH2:4]1>CO.[Pd]>[CH3:1][O:2][C@H:3]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[N:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=2)[CH2:4]1

Participants

4

Reactant 1

HCID 903587862-((S)-3-Methoxy-pyrrolidin-1-ylmethyl)-5-nitro-pyridine

Product 1

HCID 90359314HCID 90359314, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 32 (0.25 g, 1.05 mmol) in MeOH (6 mL) was hydrogenated using 10% Pd/C (50 mg) under a hydrogen atmosphere (balloon pressure) at rt for 1 h. The reaction mixture was filtered through a Celite bed and the filtrate was evaporated to give the desired amine (0.2 g, 82%) as brown liquid. Rf: 0.1 (10% MeOH/DCM); m/z): 208 [MH]+; 1H NMR (400 MHz, DMSO-d6): δ 7.82 (1H, d, J=2.4 Hz), 7.01-6.99 (1H, m), 6.88-6.86 (1H, m), 5.16 (2H, br s), 3.93-3.80 (3H, m), 3.21-3.13 (5H, m), 2.65-2.61 (1H, m), 2.42-2.34 (2H, m), 1.99-1.92 (1H, m).

Workup

  1. customat rt
  2. customfor 1 h
  3. filtrationThe reaction mixture was filtered through a Celite bed
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f8c86f562c5d4fe5a7d40ab387a41f3e
Source dataset
uspto-grants-2016_09
Patent number
US09433622B2

Reaction notes

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