Sodium Hydroxide → 3beta-Benzoyloxy-14alpha-cyano-4,4-dimethyl-5alpha-cholestan-7-ol

HRID 1493665Notes

Reaction equation

HRID 1493665 reaction equation
[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][C:14](=[O:37])[C:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C:16]=3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]1([CH3:39])[CH3:38])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:40]#[N:41].C([Al+]CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:1]([O:9][C@H:10]1[CH2:34][CH2:33][C@@:32]2([CH3:35])[C@@H:12]([CH2:13][CH:14]([OH:37])[C@@H:15]3[C@@H:31]2[CH2:30][CH2:29][C@@:28]2([CH3:36])[C@@:16]3([C:40]#[N:41])[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:27])[CH2:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]1([CH3:39])[CH3:38])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 151687573beta-Benzoyloxy-4,4-dimethyl-5alpha-cholest-8(14)-en-7-oneHCID 16686413Diethyl aluminum cyanide

Product 1

HCID 679240793beta-Benzoyloxy-14alpha-cyano-4,4-dimethyl-5alpha-cholestan-7-olYield 85.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3β-benzoyloxy-4,4-dimethyl-5α-cholest-8(14)-en-7-one (5 g, 9.4 mmole) in toluene (75 mL) at 0° C. under an argon atmosphere was treated with a solution of diethyl aluminum cyanide (1.4 M in toluene, 12.7 mL, 17 mmole). The reaction mixture was stirred at 0° C. for 0.5 hours, poured into 1N sodium hydroxide solution and extracted with methylene chloride. The organic phase was washed with water, dried and concentrated to one half the volume. An equal volume of methanol was added, the mixture was placed in a cold water bath and sodium borohydride (0.75 g) was added in portions. The mixture was stirred for 0.5 hours at ambient temperature, poured into brine, the layers separated and the organic layer was dried and concentrated to give 4.5 g (85%) of 3β-benzoyloxy-14α-cyano-4,4-dimethyl-5α-cholestan-7-ol; mp 270°-271° C. (from CH2Cl2 ).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated to one half the volume
  5. additionAn equal volume of methanol was added
  6. customthe mixture was placed in a cold water bath
  7. additionsodium borohydride (0.75 g) was added in portions
  8. stirringThe mixture was stirred for 0.5 hours at ambient temperature
  9. additionpoured into brine
  10. customthe layers separated
  11. customthe organic layer was dried
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-b0d2fad933b94dfe8c77f2d25b01983f
Source dataset
uspto-grants-1991_06
Patent number
US05023250

Reaction notes

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