Ammonium Chloride → HCID 15871122, compound

HRID 1816506Notes

Reaction equation

HRID 1816506 reaction equation
CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[CH3:15][C@@:16]12[CH2:40][C:39](=[O:41])[CH2:38][CH2:37][C@:36]1([CH3:42])[C:35]1[CH2:34][CH2:33][C@@:32]3([CH3:43])[C@@H:20]([CH2:21][CH2:22][C@@H:23]3[C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:19]=1[CH2:18][CH2:17]2.[Cl-].[NH4+]>O1CCCC1>[CH3:15][C@@:16]12[CH2:40][C@H:39]([OH:41])[CH2:38][CH2:37][C@:36]1([CH3:42])[C:35]1[CH2:34][CH2:33][C@@:32]3([CH3:43])[C@@H:20]([CH2:21][CH2:22][C@@H:23]3[C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:19]=1[CH2:18][CH2:17]2.[CH3:15][C@@:16]12[CH2:40][C@@H:39]([OH:41])[CH2:38][CH2:37][C@:36]1([CH3:42])[C:35]1[CH2:34][CH2:33][C@@:32]3([CH3:43])[C@@H:20]([CH2:21][CH2:22][C@@H:23]3[C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:19]=1[CH2:18][CH2:17]2

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 15871128HCID 15871128, compound

Product 2

HCID 15871122HCID 15871122, compoundHCID 15871123HCID 15871123, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.31 ml of a K-Selectride solution (1 N, in tetrahydrofuran) are added to a solution of 63 mg 5-methyl-5β-cholest-8-en-3-one in 4.4 ml tetrahydrofuran at −65° C. After being stirred for 2 hours the reaction mixture is allowed to warm to room temperature, poured into saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer is separated, washed with brine, dried over anhydrous sodium sulphate and filtered. After evaporation of the solvent the residue is chromatographed with a mixture of dichloromethane and acetone to give 26 mg 5-methyl-5β-cholest-8-en-3α-ol and 21 mg 5-methyl-5β-cholest-8-en-3β-ol as white solids.

Workup

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

Sources & evidence

ORD record
ord-40c6b9ce5eea41b3bdf55daf98f48c09
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

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