Dichloromethane → 2-Butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1894990Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894990
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH:15]([CH2:17][CH3:18])C)[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:19](Cl)Cl>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:15][CH2:17][CH2:18][CH3:19])[CH:13]=[O:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

3

Edukt 2

HCID 6344Dichloromethane2×HCID 666880752-2-Butyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 866208582-Butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl esterAusbeute 48 %

Versuchsvorschrift

To a stirred solution of 2-2-butyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.763 g, ca. 2.95 mmol) in DCM (30 mL) at 0° C. under nitrogen was added DMP (2.50 g, 5.90 mmol) in a single portion then the reaction mixture was warmed to ambient temperature. After 14 h the reaction mixture was diluted with DCM (70 mL), washed with 1 N NaOH (2×30 mL) and brine (30 mL) then dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (silica, 10-20% EtOAc in hexanes) gave 2-butyl-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.359 g, 1.41 mmol, 48%) as a pale yellow oil.

Aufarbeitung

  1. washwashed with 1 N NaOH (2×30 mL) and brine (30 mL)
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (silica, 10-20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a8da127ae810498cb18e857f22e231b1
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513425B2

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