N,N-Dimethylethylenediamine → 3-(N-(N',N'-dimethylaminoethane)carbamoyl)cholesterol

HRID 1836923Notes

Reaction equation

HRID 1836923 reaction equation
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:31])[CH2:14][CH2:15][CH:16]3[C@@:21]4([CH3:30])[CH2:22][CH2:23][CH:24]([O:26][C:27](Cl)=[O:28])[CH2:25][C:20]4=[CH:19][CH2:18][CH:17]3[CH:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][NH2:36]>>[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:31])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:30])[CH2:22][CH2:23][C@H:24]([O:26][C:27]([NH:36][CH2:35][CH2:34][N:33]([CH3:37])[CH3:32])=[O:28])[CH2:25][C:20]4=[CH:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 54236888C28H45ClO2

Product 1

HCID 1152343-(N-(N',N'-dimethylaminoethane)carbamoyl)cholesterol

Procedure

A solution of cholesteryl chloroformate (2.25 g, 5 mmol in 5 ml of dry chloroform) is added dropwise to an excess of a solution of N,N-dimethylethylenediamine (2 ml, 18.2 mmol, in 3 ml of dry chloroform) at 0° C. After extraction of the solvent by evaporation, the residue is purified by 2 successive recrystallizations in absolute ethanol at 4° C., and dried under vacuum. 0.545 g of DC chol is thereby obtained in the form of a white powder. The structure of the compound was verified by NMR and mass spectrometry. The results obtained are in agreement with the data published in the paper cited above.

Workup

  1. extractionAfter extraction of the solvent
  2. customby evaporation
  3. customthe residue is purified by 2 successive recrystallizations in absolute ethanol at 4° C.
  4. customdried under vacuum
  5. custom0.545 g of DC chol is thereby obtained in the form of a white powder
  6. customThe results obtained

Sources & evidence

ORD record
ord-675bae863c144eda86025cce06c2d6d4
Source dataset
uspto-grants-2004_08
Patent number
US06780421B1

Reaction notes

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