2-Nitropropane → 1-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one

HRID 1436869ノート

反応式

HRID 1436869 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]([CH:19]([CH3:21])[CH3:20])([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]([C:19]([CH3:21])([N+:16]([O-:18])=[O:17])[CH3:20])[CH2:9][C:8]2=[O:13])=[CH:14][CH:15]=1

参加物

4

反応物 3

HCID 3982-NitropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 690647451-(4-Fluorobenzyl)-5,6-dihydropyridin-2-(1H)-one

生成物 1

HCID 690609141-(4-Fluorobenzyl)-4-(1-methyl-1-nitroethyl)piperidin-2-one

実験手順

To a solution 1-(4-fluorobenzyl)-5,6-dihydropyridin-2(1H)-one (see Step 3 of Example 1) (0.75 g, 3.65 mmol) in 2-nitropropane (9.77 g, 109 mmol) was added DBU (0.56 g, 3.65 mmol). After stirring for 48 hours, the reaction mixture was concentrated under vacuum. The residual material was purified using silica gel column chromatography eluting with CH2Cl2. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.44 (m, 2H), 7.04 (t, J=9 Hz, 2H), 4.64 (d, J=15 Hz, 1H), 4.43 (d, J=15 Hz, 1H), 3.23 (m, 2H), 2.56 (m, 2H), 2.22 (m, 1H), 1.73 (m, 1H), 1.56 (s, 6H), 1.51 (m, 1H) ppm. ES MS M+1=295.

後処理

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customThe residual material was purified
  3. washeluting with CH2Cl2
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-a9c671114a434efc93b4995a40acbdbb
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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