Ammonia → HCID 12804608, compound

HRID 223432Notes

Reaction equation

HRID 223432 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH:14]1([NH:20][C@@H:21]2[CH2:38][C@@:36]3([CH3:37])[C@@H:32]([CH2:33][CH2:34][C@@H:35]3[C:39]([O:41][CH3:42])=[O:40])[C@H:31]3[C@H:22]2[C@:23]2([CH3:44])[C@@H:28]([CH2:29][CH2:30]3)[CH2:27][C@@H:26]([OH:43])[CH2:25][CH2:24]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.O.N>CC(C)=O.CCOCC>[CH:14]1([NH:20][C@@H:21]2[CH2:38][C@@:36]3([CH3:37])[C@@H:32]([CH2:33][CH2:34][C@@H:35]3[C:39]([O:41][CH3:42])=[O:40])[C@H:31]3[C@H:22]2[C@:23]2([CH3:44])[C@@H:28]([CH2:29][CH2:30]3)[CH2:27][C:26](=[O:43])[CH2:25][CH2:24]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 12804605HCID 12804605, compoundHCID 131709961Jones' reagent

Product 1

HCID 12804608HCID 12804608, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

Jones reagent was added dropwise to a stirred solution of methyl 11α-cyclohexylamino-3β-hydroxy-5α-androstane-17β-carboxylate (300 mg) in acetone (40 ml) until the reagent colour was not discharged. Water (200 ml) was added and the mixture was brought to pH 10 with 0.88 NH3 solution. Ether (50 ml) was added and the mixture was filtered. The aqueous phase was separated, extracted with ether (50 ml) and the organic phase was washed with water, dried and evaporated to leave an oil (289 mg) which crystallised from petrol to give the title compound m.p. 93°-94° C., [α]D -12°.

Workup

  1. filtrationthe mixture was filtered
  2. customThe aqueous phase was separated
  3. extractionextracted with ether (50 ml)
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-6a2443d928514ed3954cda988619be41
Source dataset
uspto-grants-1982_10
Patent number
US04353898

Reaction notes

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