Water → 17beta-Methylamino-androst-5-ene-3beta,16alpha-diol

HRID 1065698Notes

Reaction equation

HRID 1065698 reaction equation
[OH-].[Na+].C([O:6][C@H:7]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C:9](=[CH:10][CH2:11][C@@H:12]3[C@@H:21]2[CH2:20][CH2:19][C@@:17]2([CH3:18])[C@H:13]3[CH2:14][C@@H:15]([OH:28])[C@@H:16]2[NH:26][CH3:27])[CH2:8]1)(=O)C.O>C(O)C>[CH3:27][NH:26][C@H:16]1[C@H:15]([OH:28])[CH2:14][C@H:13]2[C@H:12]3[C@H:21]([CH2:20][CH2:19][C@:17]12[CH3:18])[C@:22]1([CH3:25])[C:9]([CH2:8][C@@H:7]([OH:6])[CH2:24][CH2:23]1)=[CH:10][CH2:11]3

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 12962048HCID 12962048, compound

Product 1

HCID 1296205117beta-Methylamino-androst-5-ene-3beta,16alpha-diol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide solution (1.63 ml; 4 N) was added to a solution of 17β-methylamino-androst-5-ene-3β,16α-diol 3-acetate (1.63 g) in ethanol (32.6 ml) and the resultant solution was refluxed for 1 h. Water (350 ml) was added and the precipitated crude product was filtered off and washed with water. The product was dissolved in a mixture of dichloromethane-methanol (≈1:1) and treated with charcoal. After filtration through dicalite, the filtrates were evaporated to dryness and the resultant offwhite solid was crystallised from methanol-dichloromethane-ether to give pure 17β-methylamino-androst-5-ene-3β,16α-diol as needles (1.25 g; 86.8%), m.p. 241°-246° C. (decomp.), [α]D -100.2° (c 0.93 in pyridine).

Workup

  1. customthe precipitated crude product
  2. filtrationwas filtered off
  3. washwashed with water
  4. dissolutionThe product was dissolved in a mixture of dichloromethane-methanol (≈1:1)
  5. additiontreated with charcoal
  6. filtrationAfter filtration through dicalite
  7. customthe filtrates were evaporated to dryness
  8. customthe resultant offwhite solid was crystallised from methanol-dichloromethane-ether

Sources & evidence

ORD record
ord-34ae7cbd013b476291d03205f5dedae8
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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