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

HRID 2191392Notes

Reaction equation

HRID 2191392 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]>ClCCl>[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

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 54236888C28H45ClO2

Product 1

HCID 1152343-(N-(N',N'-dimethylaminoethane)carbamoyl)cholesterolYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cholesteryl chloroformate (3 g, 6.7 mmoles) in 5 mL dry dichloromethane was added dropwise to a solution of N,N-dimethylethylene diamine (24 mmoles) in 4 mL dry dichloromethane at 0° C. The reaction was allowed to stir overnight. The solvent was then evaporated on a rotary evaporator and the residue was purified by recrystallisation from absolute ethanol to give a white solid (0.84 g, 25% yield, Rf=0.5 in 30% methanol in chloroform).

Workup

  1. customThe solvent was then evaporated on a rotary evaporator
  2. customthe residue was purified by recrystallisation from absolute ethanol
  3. customto give a white solid (0.84 g, 25% yield, Rf=0.5 in 30% methanol in chloroform)

Sources & evidence

ORD record
ord-25f3d14b60e14f849ce6518e94ac31c4
Source dataset
uspto-grants-2012_12
Patent number
US08329681B2

Reaction notes

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