Pyridine → HCID 68142511, compound

HRID 1657497Notes

Reaction equation

HRID 1657497 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH2:8][C@@H:9]2[C@@H:25]([C@:26]3([CH3:33])[C:31]=1[CH2:30][C@@H:29]([OH:32])[CH2:28][CH2:27]3)[CH2:24][CH2:23][C@@:22]1([CH3:34])[C@H:10]2[CH2:11][CH2:12][C@@H:13]1[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:4][CH3:5])[CH3:2].N1C=CC=CC=1.[C:41](Cl)(=[O:44])[CH2:42][CH3:43].C(=O)(O)[O-].[K+]>O>[CH2:4]([N:3]([CH2:6][C:7]1[CH2:8][C@@H:9]2[C@@H:25]([C@:26]3([CH3:33])[C:31]=1[CH2:30][C@@H:29]([O:32][C:41](=[O:44])[CH2:42][CH3:43])[CH2:28][CH2:27]3)[CH2:24][CH2:23][C@@:22]1([CH3:34])[C@H:10]2[CH2:11][CH2:12][C@@H:13]1[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:19])[CH3:20])[CH2:1][CH3:2])[CH3:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 191548(1R,3aS,3bS,7S,9aR,9bS,11aR)‐5‐[(Diethylamino)methyl]‐9a,11a‐dimethyl‐1‐[(2R)‐6‐ methylheptan‐2‐yl]‐ 1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH‐cyclopenta[a]phenanthren‐7‐olHCID 516893Potassium Bicarbonate

Product 1

HCID 68142511HCID 68142511, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 10 parts of 6-(diethylaminomethyl)cholest-5-en-3β-ol in 40 parts of pyridine at 0° is added, slowly and with stirring, 5 parts of propionyl chloride. When the addition is complete, stirring is continued for 2 hours while the reaction mixture warms to room temperature, whereupon 100 parts of water and 100 parts of aqueous 5% potassium bicarbonate are consecutively mixed in. 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, affording 6-(diethylaminomethyl)-3β-(propionyloxy)cholest-5-ene as the residue.

Workup

  1. additionWhen the addition
  2. stirringstirring
  3. additionare consecutively mixed in
  4. extractionThe oil which separates is extracted with hexane
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationstripped of solvent by vacuum distillation

Sources & evidence

ORD record
ord-400ce63836d14681b6213510c204913a
Source dataset
uspto-grants-1976_06
Patent number
US03960904

Reaction notes

Loading…