Dichloromethane → 3beta-Acetoxy-6-[di(2-ethoxyethyl)aminomethyl]cholest-5-ene

HRID 1657499Notes

Reaction equation

HRID 1657499 reaction equation
[C:1]([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C:7](=[C:8]([CH2:32]Br)[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])[CH3:2].[CH2:34]([O:36][CH2:37][CH2:38][NH:39][CH2:40][CH2:41][O:42][CH2:43][CH3:44])[CH3:35].ClCCl>O>[C:1]([O:4][C@H:5]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C:7](=[C:8]([CH2:32][N:39]([CH2:40][CH2:41][O:42][CH2:43][CH3:44])[CH2:38][CH2:37][O:36][CH2:34][CH3:35])[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])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 547396Bis(2-ethoxyethyl)amineHCID 545435203beta-Acetoxy-6-(bromomethyl)cholest-5-ene

Product 1

HCID 540050953beta-Acetoxy-6-[di(2-ethoxyethyl)aminomethyl]cholest-5-ene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10 parts of 3β-acetoxy-6-(bromomethyl)cholest-5-ene and 20 parts of bis(ethoxyethyl)amine in 13 parts of dichloromethane is allowed to stand at room temperatures for 24 hours, whereupon 5 volumes of water is introduced and the oil which separates is extracted with diethyl ether. The extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation to give 3β-acetoxy-6-[di(2-ethoxyethyl)aminomethyl]cholest-5-ene as the residue. The product, an oil, has the formula ##SPC9##

Workup

  1. additionis introduced
  2. extractionthe oil which separates is extracted with diethyl ether
  3. washThe extract is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationstripped of solvent by vacuum distillation

Sources & evidence

ORD record
ord-c1e772f9a8ac4b71b334e2894178d4a2
Source dataset
uspto-grants-1976_06
Patent number
US03960904

Reaction notes

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