Hydrochloric Acid → HCID 15871116, compound

HRID 2187290Notes

Reaction equation

HRID 2187290 reaction equation
[BH4-].[Na+].[C:3]([C@:5]12[CH2:29][C:28](=[O:30])[CH2:27][CH2:26][C@:25]1([CH3:31])[C:24]1[CH2:23][CH2:22][C@@:21]3([CH3:32])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@H:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:8]=1[CH2:7][CH2:6]2)#[N:4].Cl>C(O)C>[C:3]([C@:5]12[CH2:29][C@@H:28]([OH:30])[CH2:27][CH2:26][C@:25]1([CH3:31])[C:24]1[CH2:23][CH2:22][C@@:21]3([CH3:32])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@H:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:8]=1[CH2:7][CH2:6]2)#[N:4].[C:3]([C@:5]12[CH2:29][C@H:28]([OH:30])[CH2:27][CH2:26][C@:25]1([CH3:31])[C:24]1[CH2:23][CH2:22][C@@:21]3([CH3:32])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@H:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:8]=1[CH2:7][CH2:6]2)#[N:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 15871126HCID 15871126, compound

Product 2

HCID 15871116HCID 15871116, compoundHCID 15871117HCID 15871117, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

327 mg sodium borohydride are added to a solution of 1.76 g 5-cyano-5α-cholest-8-en-3-one in 200 ml ethanol at room temperature. The reaction mixture is stirred for 4 hours. After addition of hydrochloric acid (1 N) the resulting mixture is extracted with dichloromethane. The organic layer is separated, dried over anhydrous sodium sulphate and filtered. After evaporation of the solvent the residue is chromatographed with a mixture of hexane and ethyl acetate to give 0.36 mg 5-cyano-5α-cholest-8-en-3β-ol and 1.00 g 5-cyano-5α-cholest-8-en-3α-ol as white solids.

Workup

  1. extractionis extracted with dichloromethane
  2. customThe organic layer is separated
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customAfter evaporation of the solvent the residue
  6. customis chromatographed with a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-6efdd39343b14e8b9d86cd838f973c86
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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