HCID 86735464, compound → HCID 86735465, compound

HRID 616340Notes

Reaction equation

HRID 616340 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[OH:5][C@H:6]1[CH2:11][CH2:10][C@H:9]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:7]12[CH3:8])[C@@H:20]1[C:15]([CH2:16][C:17](=[O:24])[CH2:18][CH2:19]1)=[CH:14][C@H:13]3[CH3:25]>O1CCCC1>[C:1]([OH:4])(=[O:3])[CH3:2].[CH3:25][C@@H:13]1[CH:14]=[C:15]2[C@H:20]([CH2:19][CH2:18][C@H:17]([OH:24])[CH2:16]2)[C@@H:21]2[C@@H:12]1[C@H:9]1[C@@:7]([CH2:23][CH2:22]2)([CH3:8])[C@@H:6]([OH:5])[CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 86735464HCID 86735464, compound

Product 1

HCID 86735465HCID 86735465, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17β-hydroxy-7α-methyl-estr-5-en-3-one acetate dissolved in tetrahydrofuran is purged with nitrogen and slowly added to a suspension of lithium tertiarybutoxyaluminum hydride also purged with nitrogen. The mixture is stirred at room temperature for about 16 hours and excess hydride is destroyed by cautiously adding a solution of sodium potassium tartrate. The solid which forms is removed by filtration and the filtrate is extracted with methylene chloride. The combined methylene chloride extracts are washed with water, dried and concentrated under vacuum. Recrystalization of the residue from acetone-hexane yields the desired 7α-methyl-estr-5-ene-3β,17β-diol acetate.

Workup

  1. customis purged with nitrogen
  2. additionslowly added to a suspension of lithium tertiarybutoxyaluminum hydride
  3. customalso purged with nitrogen
  4. customexcess hydride is destroyed
  5. additionby cautiously adding a solution of sodium potassium tartrate
  6. customThe solid which forms is removed by filtration
  7. extractionthe filtrate is extracted with methylene chloride
  8. washThe combined methylene chloride extracts are washed with water
  9. customdried
  10. concentrationconcentrated under vacuum
  11. customRecrystalization of the residue from acetone-hexane

Sources & evidence

ORD record
ord-21c73b8191d64ff08969a1bfe28bd331
Source dataset
uspto-grants-1978_02
Patent number
US04073899

Reaction notes

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