Sodium borohydride → HCID 10236953, compound

HRID 551843Notes

Reaction equation

HRID 551843 reaction equation
[C:1]([C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][C:9](=[O:25])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)([O:3][CH3:4])=[O:2].[BH4-].[Na+]>ClCCl.CO>[C:1]([C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH:9]([OH:25])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[OH:24])[CH2:6]1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 10286773HCID 10286773, compound

Product 1

HCID 10236953HCID 10236953, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

3β-Carbomethoxyandrost-5-ene-7,17-dione (42) (0.5 g, 0.0014 mol) was dissolved in a mixture of dichloromethane (5 mL) and methanol (10 mL). The mixture was stirred at room temperature and finely powdered sodium borohydride (0.16 g, 0.004 mol) was added slowly. After 15 min the reaction mixture was quenched with water and the product was extracted with methylene dichloride. The organic layer was washed, dried and solvent removed. The product was crystallized from acetone-petroleum ether to afford 0.35 g (70%) of 3β-carbomethoxyandrost-5-ene-7,17β-diol (49) as a white crystalline solid, m.p. 150-52° C. LC-MS and 1H NMR analysis of the product showed a 8:2 ratio of isomeric 7β-hydroxy and 7α-hydroxy compound.

Workup

  1. customAfter 15 min the reaction mixture was quenched with water
  2. extractionthe product was extracted with methylene dichloride
  3. washThe organic layer was washed
  4. customdried
  5. customsolvent removed
  6. customThe product was crystallized from acetone-petroleum ether

Sources & evidence

ORD record
ord-115b29bbb39542c79d303ed9e42c4038
Source dataset
uspto-grants-2011_05
Patent number
US07947846B2

Reaction notes

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