1-Nitropropane → HCID 69068115, compound

HRID 1436880Notes

Reaction equation

HRID 1436880 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]=[CH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.[N+:16]([CH2:19][CH2:20][CH3:21])([O-:18])=[O:17].C1CCN2C(=NCCC2)CC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH:19]([N+:16]([O-:18])=[O:17])[CH2:20][CH3:21])[CH2:9][C:8]2=[O:13])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 79031-NitropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

Product 1

HCID 69068115HCID 69068115, compound

Procedure

To a solution 1-(4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-one (2.0 g, 10 mmol) in 1-nitropropane (8.68 g, 97.5 mmol) was added DBU (1.48 g, 9.75 mmol). After stirring for 24 hours, the reaction mixture was concentrated under vacuum. The residual material was purified by silica gel column chromatography eluting with 1% methanol in CH2Cl2. The appropriate fractions were combined and concentrated to afford the title compound as mixture of diastereomers. The diastereomers co-eluted with a retention time of 3.01 min. The HPLC method was performed on a Hewlett-Packard Zorbax SB-C8 column (75×4.6 mm, 3.5 micron) eluting with 5%-100% CH3CN (0.1% TFA) in H2O (0.1% TFA). ES MS M+1=295.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customThe residual material was purified by silica gel column chromatography
  3. washeluting with 1% methanol in CH2Cl2
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5c939d823407476598573d2e5de72bf4
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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