Nitromethane → 1-(4-Fluorobenzyl)-4-(nitromethyl)piperidin-2-one

HRID 1436867ノート

反応式

HRID 1436867 の反応式
[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]([CH3:19])([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]([CH2:19][N+:16]([O-:18])=[O:17])[CH2:9][C:8]2=[O:13])=[CH:14][CH:15]=1

参加物

4

反応物 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

生成物 1

HCID 690699721-(4-Fluorobenzyl)-4-(nitromethyl)piperidin-2-one

実験手順

To a solution of 1-(4-fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one (6.2 g, 30 mmol) in nitromethane (64.5 g, 1.06 mol) under an atmosphere of nitrogen was added DBU (4.59 g, 30.2 mmol). The reaction mixture was stirred overnight at room temperature. The product mixture was concentrated under vacuum. The residue was purified using column chromatography on silica gel eluting with 50%-100% ethyl acetate in hexanes. Collection and concentration of appropriate fractions provided the title compound as pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.25 (m, 2H), 7.01 (t, J=8.7 Hz, 2H), 4.64 (d, J=14.6 Hz, 1H), 4.48 (d, J=14.5 Hz, 1H), 4.34 (m, 2H), 3.27 (m, 2H), 2.23 (dd, J=17, 10.6 Hz, 1H), 2.0 (m, 1H), 1.61 (m, 1H).

後処理

  1. concentrationThe product mixture was concentrated under vacuum
  2. customThe residue was purified
  3. customCollection and concentration of appropriate fractions

出典と根拠

ORDレコード
ord-3f6921c30afc4616b0b754fb78c277a4
出典データセット
uspto-grants-2009_11
特許番号
US07619086B2

反応ノート

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