Nitromethane → HCID 66598306, compound

HRID 1483794Notes

Reaction equation

HRID 1483794 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH3:15][N+:16]([O-:18])=[O:17].C1CCN2C(=NCCC2)CC1>>[N+:16]([CH2:15][CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:2](=[O:1])[CH2:7]1)([O-:18])=[O:17]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66598173tert-Butyl 6-oxo-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 66598306HCID 66598306, compoundYield 22%

Procedure

A solution of tert-butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate (2.1 g, 11 mmol) in CH3NO2 (22.7 g, 372 mmol) under N2 was added DBU (2.52 g, 16.5 mmol). The mixture was stirred at room temperature overnight and then condensed and purified by flash chromatography to give compound tert-butyl 4-(nitromethyl)-2-oxopiperidine-1-carboxylate (0.6 g, 22%) as a white solid.

Workup

  1. customcondensed
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-720bd792645a4197ac1dc0910522ee0f
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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