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

HRID 722729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722729
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f2c70e3d2c494061988d2294975c765f
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138395B2

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