Sodium borohydride → 3beta-Carboethoxyandrost-5-ene-7beta,17beta-diol

HRID 551844Notes

Reaction equation

HRID 551844 reaction equation
[C:1]([C@H:6]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:8](=[CH:9][C:10](=[O:26])[C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:25])[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>ClCCl.CO>[C:1]([C@H:6]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:8](=[CH:9][C@H:10]([OH:26])[C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[OH:25])[CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 102370863beta-Carboethoxyandrost-5-ene-7,17-dioneHCID 21585214Cerium trichloride heptahydrate

Product 1

HCID 101724223beta-Carboethoxyandrost-5-ene-7beta,17beta-diolYield 75.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3β-Carbomethoxyandrost-5-ene-7,17-dione (44) (0.3 g, 0.8 mmol) in 5 mL dichloromethane and 10 mL methanol was treated with cerium (III) chloride heptahydrate (0.3 g, 0.8 mmol). To this cold solution, finely powdered sodium borohydride (0.09 g, 2.4 mmol) was added slowly. After 15 minutes the solvent was evaporated to complete dryness, the solid crude was taken up in dichloromethane, stirred for 30 minutes and filtered on a small bed of celite. The organic layer was washed once with water, dried and the solvent was removed. The product was crystallized from acetone-petroleum ether to afford 0.22 g (73%) of 3β-carboethoxyandrost-5-ene-7β,17β-diol (50) as a white solid, m.p. 170-71° C.

Workup

  1. customAfter 15 minutes the solvent was evaporated
  2. filtrationfiltered on a small bed of celite
  3. washThe organic layer was washed once with water
  4. customdried
  5. customthe solvent was removed
  6. customThe product was crystallized from acetone-petroleum ether

Sources & evidence

ORD record
ord-fd50dbe4e9c84d5883696e6b6fb09967
Source dataset
uspto-grants-2011_05
Patent number
US07947846B2

Reaction notes

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