Potassium Hydroxide → HCID 12961951, compound

HRID 1065692Notes

Reaction equation

HRID 1065692 reaction equation
[OH-].[K+].[C:3]([N:6](C)[C@H:7]1[C@@H:12]([OH:13])[CH2:11][C@H:10]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:8]12[CH3:9])[C@:22]1([CH3:23])[C@H:17]([CH2:18][C@@H:19]([OH:27])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3)(=O)C>C(O)C>[CH3:3][NH:6][C@H:7]1[C@@H:12]([OH:13])[CH2:11][C@H:10]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:8]12[CH3:9])[C@:22]1([CH3:23])[C@H:17]([CH2:18][C@@H:19]([OH:27])[CH2:20][CH2:21]1)[CH2:16][CH2:15]3

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86738376HCID 86738376, compound

Product 1

HCID 12961951HCID 12961951, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium hydroxide (4.8 ml; 10 N) was added to a stirred suspension of 17β-(N-acetyl-methylamino)-5α-androstane-3β,16β-diol (4.8 g) in ethanol (96 ml) and the stirred mixture was heated under reflux for 2 h. A clear solution was obtained after 5 min., and a solid product precipitated after 30 min. The mixture was cooled, water was added, followed by brine and the product was filtered off and washed with water. Crystallisation from aqueous ethanol gave 17β-methylamino-5α-androstane-3β,16β-diol as prisms (3.5 g), m.p. 241°-253° C.

Workup

  1. temperaturethe stirred mixture was heated
  2. temperatureunder reflux for 2 h
  3. customA clear solution was obtained after 5 min.
  4. customa solid product precipitated after 30 min
  5. temperatureThe mixture was cooled
  6. additionwater was added
  7. filtrationthe product was filtered off
  8. washwashed with water
  9. customCrystallisation from aqueous ethanol

Sources & evidence

ORD record
ord-9eeea7c921ae494b9541cafa619d953c
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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