Water → HCID 70502497, compound

HRID 543644Notes

Reaction equation

HRID 543644 reaction equation
[OH-].[Na+].C([O:6][C@H:7]1[CH2:24][C@@:23]2([CH3:25])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[CH2:21][CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][C@H:16]([N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[C@@H:17]2[OH:26])[CH2:9][CH2:8]1)(=O)C.O>CO>[N:27]1([C@H:16]2[CH2:15][C@H:14]3[C@H:13]4[C@H:22]([CH2:21][CH2:20][C@:18]3([CH3:19])[C@H:17]2[OH:26])[C@:23]2([CH3:25])[C@H:10]([CH2:9][CH2:8][C@@H:7]([OH:6])[CH2:24]2)[CH2:11][CH2:12]4)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70501595HCID 70501595, compound

Product 1

HCID 70502497HCID 70502497, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide solution (60 ml; 4N) was added to a solution of 16β-(1-piperidinyl)-5α-androstane-2β,17β-diol 2-acetate (25.49 g) in methanol (120 ml) and the mixture was heated under reflux for 1 h. When the solution had cooled to room temperature, water (200 ml) was added to precipitate the product, which was filtered off and washed with water (3×200 ml). A solution of the crude solid in diethyl ether (150 ml) was washed neutral with water (2×200 ml), dried (MgSO4) and evaporated to dryness. Crystallisation of the resulting white solid from methanol acetone afforded 16β-(1-piperidinyl)-5α-androstane-2β,17β-diol (17.51 g), m.p. 215°-219° C.; [α]D +36.1° (c 0.48 in CHCH3).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 h
  3. customto precipitate the product, which
  4. filtrationwas filtered off
  5. washwashed with water (3×200 ml)
  6. washA solution of the crude solid in diethyl ether (150 ml) was washed neutral with water (2×200 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness
  9. customCrystallisation of the resulting white solid from methanol acetone

Sources & evidence

ORD record
ord-347e360b12e94ab884c9f8f0dcd6598f
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

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