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

HRID 722729노트

반응식

HRID 722729 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f2c70e3d2c494061988d2294975c765f
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138395B2

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