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

HRID 722729Notes

Reaction equation

HRID 722729 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f2c70e3d2c494061988d2294975c765f
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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