N-(5-(Hydroxymethyl)bicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide → N-(5-Formylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide

HRID 1503251Notes

Reaction equation

HRID 1503251 reaction equation
[OH:1][CH2:2][C:3]12[CH2:10][C:7]([NH:11][C:12]([C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)=[O:13])([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:2]([C:3]12[CH2:10][C:7]([NH:11][C:12]([C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)=[O:13])([CH2:8][CH2:9]1)[CH2:6][CH2:5][CH2:4]2)=[O:1]

Participants

4

Reactant 2

HCID 117702464N-(5-(Hydroxymethyl)bicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamideHCID 178418287HCID 178418287, compound

Product 1

HCID 117702640N-(5-Formylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamideYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(5-(hydroxymethyl)bicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide (540 mg, 2.1 mmol) in DCM (20 mL) was added PCC (670 mg, 3.1 mmol) in portions and the reaction mixture was stirred at room temperature for two hours. The mixture was filtered through a pad of silica gel and the filtrate was concentrated. The resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2/1) to yield 350 mg (65%) of the title compound, N-(5-formylbicyclo[3.2.1]octan-1-yl)pyrazine-2-carboxamide, as a white solid. ESI-MS m/z: 260 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a pad of silica gel
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-6b5e3116dd1a41dbb3ad1f295e86afcc
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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