4-Benzylpiperidine → 4-Benzyl-1-(3-hydroxy-1-methylpropyl)piperidine

HRID 324553

反応式

HRID 324553 の反応式
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:21])[CH2:15][C:16](OCC)=[O:17])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1CCNCC1)C1C=CC=CC=1.C(OCC)(=O)/C=C/C>C(O)(C)C>[CH2:1]([CH:8]1[CH2:9][CH2:10][N:11]([CH:14]([CH3:21])[CH2:15][CH2:16][OH:17])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 317384-BenzylpiperidineHCID 429065Ethyl trans-crotonateHCID 18621512Ethyl 3-(4-benzylpiperidin-1-yl)butyrate

生成物 1

HCID 129729654-Benzyl-1-(3-hydroxy-1-methylpropyl)piperidine収率 74%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

Ethyl 3-(4-benzylpiperidin-1-yl)butyrate. A solution of 4-benzyl piperidine (0.50 mL, 2.8 mmol) and ethyl crotonate (0.46 mL, 3.4 mol) in isopropanol (10 mL) was refluxed for 24 h and was concentrated in vacuo. The crude compound was purified by filtration on silica gel using CH2Cl2/MeOH as solvent to afford the title compound as a pale yellow oil (0.64 g, 74%): 1H NMR (CDCl3) δ 1.09 (d, J=6.6 Hz, 3H), 1.30 (t, J=6.9 Hz, 3H), 1.20-1.40 (m, 2H), 1.45-1.61 (m, 1H), 1.68 (bd, J=12.3 Hz, 2H), 2.10-2.35 (m, 3H), 2.57 (d, J6.9 Hz, 2H), 2.50-2.70 (m, 1H), 2.82 (bd, J=10.8 Hz, 2H), 3.15-3.30 (m, 1H), 4.18 (q, J=6.9 Hz, 2H), 7.18 (d, J=7.2 Hz, 2H), 7.24 (m, 1H), 7.32 (t, J=6.9 Hz, 2H).

後処理

  1. concentrationwas concentrated in vacuo
  2. filtrationThe crude compound was purified by filtration on silica gel

出典と根拠

ORDレコード
ord-28e8e8180f714be6b0b0588971ac9074
出典データセット
uspto-grants-2001_04
特許番号
US06218404B1

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