HCID 70501729, compound → HCID 70501193, compound

HRID 543646Notes

Reaction equation

HRID 543646 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]([O:17][C@H:18]1[C@@H:23]([N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:22][C@H:21]2[C@H:30]3[C@H:40]([CH2:41][CH2:42][C@:19]12[CH3:20])[C@:38]1([CH3:39])[C@H:33]([CH2:34][CH2:35][C@@H:36]([OH:43])[CH2:37]1)[CH2:32][CH2:31]3)(=[O:16])[CH3:15]>CC(C)=O>[C:14]([O:17][C@H:18]1[C@@H:23]([N:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:22][C@H:21]2[C@H:30]3[C@H:40]([CH2:41][CH2:42][C@:19]12[CH3:20])[C@:38]1([CH3:39])[C@H:33]([CH2:34][CH2:35][C:36](=[O:43])[CH2:37]1)[CH2:32][CH2:31]3)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 70501729HCID 70501729, compoundHCID 131709961Jones' reagent

Product 1

HCID 70501193HCID 70501193, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
5 °C

Procedure

Jones reagent (21.0 ml; 8N) was added dropwise to a stirred suspension of 16β-(1-piperidinyl)-5α-androstane-2β,17β-diol 17-acetate (14.0 g) in acetone (250 ml), cooled to approx. 5° C. in an ice-bath. When the addition was complete, the cooling bath was removed and stirring was continued for 3 h. Saturated sodium carbonate solution (100 ml) was added to give pH approx. 9 and the product was extracted into dichloromethane (150 ml). The organic layer was separated, washed neutral with water (3×150 ml) and dried (MgSO4). The solution was concentrated while ether was added to afford 17β-acetyloxy-16β-(1-piperidinyl)-5α-androstan-2-one (12.2 g) m.p. 165°-167° C.; [α]D +44.6° (c 0.45 in CHCl3).

Workup

  1. additionWhen the addition
  2. customthe cooling bath was removed
  3. additionSaturated sodium carbonate solution (100 ml) was added
  4. customto give pH approx. 9
  5. extractionthe product was extracted into dichloromethane (150 ml)
  6. customThe organic layer was separated
  7. washwashed neutral with water (3×150 ml)
  8. dry with materialdried (MgSO4)
  9. concentrationThe solution was concentrated while ether
  10. additionwas added

Sources & evidence

ORD record
ord-f67ff3264cf34d598a04499fa6af00a0
Source dataset
uspto-grants-1984_05
Patent number
US04447425

Reaction notes

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