Thionyl Chloride → 6-Allyl-piperidine-2-carboxylic acid methyl ester

HRID 722729ノート

反応式

HRID 722729 の反応式
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH:12]=[CH2:13])[N:6]1C(OC(C)(C)C)=O)=[O:4].S(Cl)(Cl)=O>CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH:7]([CH2:11][CH:12]=[CH2:13])[NH:6]1)=[O:4]

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 670930876-Allyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

生成物 1

HCID 696594866-Allyl-piperidine-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The crude 6-allyl-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester obtained from the previous step is dissolved in MeOH (500 mL) and treated with thionyl chloride (20 mL). The solution is stirred overnight and the solvent removed in vacuo. The crude residue is dissolved in EtOAc, washed with saturated NaHCO3, dried (MgSO4), and concentrated to yield 2.1 g of the desired product. The product is used in the next step without purification. 1H NMR (CDCl3) δ 5.82 (m, 1H), 5.22–5.10 (m, 2H), 3.75 (s, 3H), 3.37 (dd, J=11.1, 2.8 Hz, 1H), 2.60 (m, 1H), 2.21 (m, 2H), 2.10–1.10 (m, 6H).

後処理

  1. customthe solvent removed in vacuo
  2. dissolutionThe crude residue is dissolved in EtOAc
  3. washwashed with saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-f2c70e3d2c494061988d2294975c765f
出典データセット
uspto-grants-2006_11
特許番号
US07138395B2

反応ノート

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