Acetone → 19-Methylthioandrost-4-ene-3alpha,17beta-diol

HRID 1086411Notes

Reaction equation

HRID 1086411 reaction equation
[BH4-].[Na+].[CH3:3][S:4][CH2:5][C@@:6]12[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C:18](=[O:24])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]1=[CH:10][C:9](=[O:25])[CH2:8][CH2:7]2.CC(C)=O.C([O-])(O)=O.[Na+]>C1COCC1.CO.C(O)(=O)C>[CH3:3][S:4][CH2:5][C@@:6]12[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[C@@H:18]([OH:24])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]1=[CH:10][C@H:9]([OH:25])[CH2:8][CH2:7]2

Participants

8

Reactant 4

HCID 180AcetoneHCID 14614219-Thiomethylandrost-4-ene-3,17-dioneHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 6792862619-Methylthioandrost-4-ene-3alpha,17beta-diolYield 79%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.6 g of NaBH4 was added to a solution of 6 g of 19-methylthioandrost-4-ene-3,17-dione in a mixture of 25 ml of THF and 25 ml of methanol. After 1/2 hour, 2 ml of acetone, followed by 5 ml of 50% acetic acid were added. After stirring for 1/2 hour, the mixture was poured out into 200 ml of 5% NaHCO3 solution. Subsequently, the product was extracted with CH2Cl2. After washing, drying and evaporating down the organic layer, the residue obtained was chromatographed using silica gel. In this manner, 4.8 g of 19-methylthioandrost-4-ene-3α,17β-diol were obtained, melting point 85°-87° C., (Rf =0.23 (toluene/ethyl acetate 7:3).

Workup

  1. additionwere added
  2. extractionSubsequently, the product was extracted with CH2Cl2
  3. washAfter washing
  4. customdrying
  5. customevaporating down the organic layer
  6. customthe residue obtained
  7. customwas chromatographed

Sources & evidence

ORD record
ord-333de724c27a4734b3ff9cb914cad499
Source dataset
uspto-grants-1991_07
Patent number
US05030627

Reaction notes

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