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

HRID 1168664Notes

Reaction equation

HRID 1168664 reaction equation
Cl[C:2]([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6]1)=[O:3].[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][NH2:36].II>C(Cl)(Cl)Cl>[CH3:22][C@@H:15]([C@@H:14]1[C@@:23]2([CH3:31])[CH2:24][CH2:25][C@@H:26]3[C@@:27]4([CH3:30])[CH2:28][CH2:29][C@H:5]([O:4][C:2]([NH:36][CH2:35][CH2:34][N:33]([CH3:37])[CH3:32])=[O:3])[CH2:6][C:7]4=[CH:8][CH2:9][C@H:10]3[C@@H:11]2[CH2:12][CH2:13]1)[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 807IodineHCID 66053N,N-DimethylethylenediamineHCID 111262Cholest-5-en-3-ol (3beta)-, 3-(carbonochloridate)

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Compound XIV was synthesized by mixing a-solution of cholesterol chloroformate (0.5 mmol) in chloroform with a solution of N,N-dimethylethylenediamine (9.1 mmol) in chloroform in a dry ice-ethanol bath. The solvent and the unreacted amine were removed in vacuo. Compound XIV was purified by two successive recrystallizations in ethanol. (Yield, 65%) TLC (chloroform:methanol=65:35) showed a single spot (Rf=0.37) when developed with iodine. The product was characterized by proton NMR.

Workup

  1. customThe solvent and the unreacted amine were removed in vacuo
  2. customCompound XIV was purified by two successive recrystallizations in ethanol
  3. custom(Yield, 65%) TLC (chloroform:methanol=65:35)

Sources & evidence

ORD record
ord-7a6cf3de51834f0abf9f5f90e1b8ee59
Source dataset
uspto-grants-2003_09
Patent number
US06627218B2

Reaction notes

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