Ammonium Chloride → Cholesta-5,7-diene-1,3-diol

HRID 1587616Notes

Reaction equation

HRID 1587616 reaction equation
[CH3:1][CH:2]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:24]([O:39]C(OC)=O)[CH2:25][C@@H:26]2[O:34]C(OC)=O)=[CH:21][CH:20]=3)[CH2:17][CH2:16]1)[CH2:3]OS(C1C=CC(C)=CC=1)(=O)=O.[Li].C([Cu]CCC(C)C)CC(C)C.[CH2:56]([Li])[CH2:57][CH:58]([CH3:60])[CH3:59].[Cl-].[NH4+]>C(OCC)C>[CH3:59][CH:58]([CH2:57][CH2:56][CH2:3][C@H:2]([C@@H:15]1[C@:32]2([CH3:33])[C@H:18]([C:19]3[C@H:29]([CH2:30][CH2:31]2)[C@:27]2([CH3:28])[C:22]([CH2:23][C@@H:24]([OH:39])[CH2:25][C@@H:26]2[OH:34])=[CH:21][CH:20]=3)[CH2:17][CH2:16]1)[CH3:1])[CH3:60]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 8674694320-Methyl-1alpha,3beta-bis(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7-dieneHCID 178445856HCID 178445856, compoundHCID 178506862HCID 178506862, compound

Product 1

HCID 193829Cholesta-5,7-diene-1,3-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

A solution of 51 mg of 20-methyl-1α,3β-bis(methoxycarbonyloxy)-21-p-toluenesulfonyloxypregna-5,7-diene in 1 ml of diethyl ether was added dropwise, at -50° C. to -60° C., to a diethyl ether solution of diisoamylcopper lithium as prepared from 100 mg of cuprous iodide and 0.9 ml of 1.1N diethyl ether solution of isoamyllithium in 2 ml of diethyl ether. reaction mixture was poured into a cold aqueous solution of ammonium chloride and the resulting mixture was extracted with diethyl ether. The extract was washed with 10% aqueous ammonia, water and an aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated. The residue was dissolved in 1 ml of methanol, 10 mg of potassium carbonate was added, and the resulting mixture was stirred at ambient temperature for 12 hours. The reaction mixture was poured into water and extracted with methylene chloride. The extract was washed with an aqueous solution of sodium chloride, dried over sodium sulfate and concentrated. The residue was washed with cold ethyl acetate to give 29 mg of cholesta-5,7-diene-1α,3β-diol.

Workup

  1. customreaction mixture
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThe extract was washed with 10% aqueous ammonia, water
  4. dry with materialan aqueous solution of sodium chloride, dried over sodium sulfate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in 1 ml of methanol
  7. addition10 mg of potassium carbonate was added
  8. additionThe reaction mixture was poured into water
  9. extractionextracted with methylene chloride
  10. washThe extract was washed with an aqueous solution of sodium chloride
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated
  13. washThe residue was washed with cold ethyl acetate

Sources & evidence

ORD record
ord-c347a723303646649374acad0c7d4d0e
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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