Acetic Acid → HCID 13187315, compound

HRID 326153Notes

Reaction equation

HRID 326153 reaction equation
[Na].[CH3:2][C:3]([C@@H:5]1[C@@:9]2([CH3:24])[CH2:10][CH2:11][C@@H:12]3[C@@:17]4([CH3:23])[CH2:18][CH2:19][C@@H:20]([NH2:22])[CH2:21][C:16]4=[CH:15][CH2:14][C@H:13]3[C@@H:8]2[CH2:7][CH2:6]1)=[O:4].C(O)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)CC.O>[NH2:22][C@@H:20]1[CH2:19][CH2:18][C@@:17]2([CH3:23])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:12]2[CH2:11][CH2:10][C@@:9]2([CH3:24])[C@H:8]3[CH2:7][CH2:6][C@@H:5]2[CH:3]([OH:4])[CH3:2])[CH2:21]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 5360545SodiumHCID 12310548(3α)-3-Aminopregn-5-en-20-one

Product 1

HCID 13187315HCID 13187315, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent2×

Procedure

To a refluxing 100 ml of propanol were simultaneously added, over a period of 20 minutes, in small portions 5 g of sodium and a solution of 5 g of holamine in 5 ml of propanol while continuing reflux. After 1 hour and 25 minutes, the temperature was returned to ambient, the mixture chilled and acidified with acetic acid to pH 6. The pH raised to pH 8 with potassium carbonate and the mixture was diluted with 500 ml of water, partially evaporated, 300 ml of water were added and the mixture was allowed to crystallize for 24 hours in the refrigerator. The filtered crystals were washed in water and dissolved in 10 ml of methylene chloride to which was added 50 ml of ethyl acetate and 30 ml of isopropyl ether. The methylene chloride was evaporated and the product allowed to crystallize during 16 hours in the refrigerator. 3 g of 3α-amino pregn-5-ene- 20-ol was obtained melting at 160°.

Workup

  1. custom25 minutes
  2. temperaturethe mixture chilled
  3. custompartially evaporated
  4. addition300 ml of water were added
  5. customto crystallize for 24 hours in the refrigerator
  6. washThe filtered crystals were washed in water
  7. dissolutiondissolved in 10 ml of methylene chloride to which
  8. additionwas added 50 ml of ethyl acetate and 30 ml of isopropyl ether
  9. customThe methylene chloride was evaporated
  10. customto crystallize during 16 hours in the refrigerator

Sources & evidence

ORD record
ord-1b7aeb12516c48dd949390b450a55e48
Source dataset
uspto-grants-1984_04
Patent number
US04444767

Reaction notes

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