Water → HCID 12961966, compound

HRID 1065700Notes

Reaction equation

HRID 1065700 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@:7]([Cl:28])([C@H:8]([Cl:27])[CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C@@H:13]([OH:26])[C@@H:14]2[NH:24][CH3:25])[CH2:6]1)(=O)C.O>CO.[OH-].[K+]>[Cl:28][C@:7]12[CH2:6][C@@H:5]([OH:4])[CH2:22][CH2:21][C@:20]1([CH3:23])[C@@H:19]1[C@H:10]([C@H:11]3[C@@:15]([CH2:17][CH2:18]1)([CH3:16])[C@@H:14]([NH:24][CH3:25])[C@H:13]([OH:26])[CH2:12]3)[CH2:9][C@H:8]2[Cl:27]

Participants

5

Reactant 2

HCID 962WaterHCID 129619645alpha,6beta-Dichloro-17beta-methylamino-5alpha-androstane-3beta,16alpha-diol 3-acetate

Product 1

HCID 12961966HCID 12961966, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14797Potassium HydroxideSolvent

Procedure

A stirred suspension of 5α,6β-dichloro-17β-methylamino-5α-androstane-3β,16α-diol 3-acetate (13 g) in methanol (105 ml) and aqueous potassium hydroxide solution (3.9 ml; 10 N) was heated under reflux for 1 hr., cooled and water was added to precipitate the product as a white solid, which was filtered off, and washed with water (wt. 11 g). Recrystallisation of a sample from methanol gave 5α,6β-dichloro-17β-methylamino-5α-androstane-3β,16α-diol as prisms, m.p. 194°-195° C. (decomp.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. temperature, cooled
  4. customto precipitate the product as a white solid, which
  5. filtrationwas filtered off
  6. washwashed with water (wt. 11 g)
  7. customRecrystallisation of a sample from methanol

Sources & evidence

ORD record
ord-3da076f15c284c6ab43a72689fd47a69
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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