Methanol → HCID 68140813, compound

HRID 1657500Notes

Reaction equation

HRID 1657500 reaction equation
C([O:4][C@H:5]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C:7](=[C:8]([CH2:36][N:37]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:9][C@@H:10]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:35])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:26])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:25])[CH2:20]OC(=O)C)[CH2:6]1)(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:38]([N:37]([CH2:36][C:8]1[CH2:9][C@@H:10]2[C@@H:30]([C@:31]3([CH3:34])[C:7]=1[CH2:6][C@@H:5]([OH:4])[CH2:33][CH2:32]3)[CH2:29][CH2:28][C@@:27]1([CH3:35])[C@H:11]2[CH2:12][CH2:13][C@@H:14]1[C@H:15]([CH3:26])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:20])[CH3:25])[CH2:42][CH2:43][CH2:44][CH3:45])[CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86733510HCID 86733510, compound

Product 1

HCID 68140813HCID 68140813, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of approximately 10 parts of 3β-acetoxy-acetoxy-6-(dibutylaminomethyl)cholest-5-ene in 80 parts of methanol is added 10 parts of aqueous 20% potassium carbonate. The resultant mixture is heated to the boiling point under reflux for 2 hours, whereupon 100 parts of water is introduced. The oil which separates is extracted with hexane. The extract is washed with water, dried over anhydrous sodium sulfate, and stripped of solvent by vacuum distillation. The residual oil is taken up in benzene; and the benzene solution is chromatographed on alumina, using benzene and mixtures thereof with increasing amounts of ethanol as developing solvents. From an eluate comprising 2% ethanol in benzene, on evaporation of solvent, 6-(dibutylaminomethyl)cholest-5-en-3β-ol is obtained as the residue.

Workup

  1. additionis introduced
  2. extractionThe oil which separates is extracted with hexane
  3. washThe extract is washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationstripped of solvent by vacuum distillation
  6. customand the benzene solution is chromatographed on alumina
  7. customFrom an eluate comprising 2% ethanol in benzene, on evaporation of solvent

Sources & evidence

ORD record
ord-c6900309c4a540ce95fcbd9642e583f1
Source dataset
uspto-grants-1976_06
Patent number
US03960904

Reaction notes

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