Sodium Bicarbonate → 1 Alpha,25-dihydroxycholesterol

HRID 1106225Notes

Reaction equation

HRID 1106225 reaction equation
O1CCCCC1[O:7][C@@H:8]1[C@@:39]2([CH3:40])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:41])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:34])[CH2:21][C:22]#[C:23][C:24]([O:27]C2CCCCO2)([CH3:26])[CH3:25])[CH2:11][C@@H:10]([O:42]C2CCCCO2)[CH2:9]1.C(=O)([O-])O.[Na+].[H][H]>C(O)C.[Ni]>[OH:7][C@@H:8]1[C@@:39]2([CH3:40])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:38]2[CH2:37][CH2:36][C@@:35]2([CH3:41])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@H:20]([CH3:34])[CH2:21][CH2:22][CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])[CH2:11][C@@H:10]([OH:42])[CH2:9]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 128511561alpha,3beta,25-tris[(tetrahydro-2H-pyran-2-yl)oxy]-cholest-5-en-23-yneHCID 178418361HCID 178418361, compound

Product 1

HCID 1911241 Alpha,25-dihydroxycholesterolYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.2 g (0.3 mmol) of 1α,3β,25-tris[(tetrahydro-2H-pyran-2-yl)oxyl]-cholest-5-en-23-yne in 10 ml of ethanol was treated with 0.05 g of sodium hydrogen carbonate and 0.4 ml of concentrated ethanolic Raney-nickel suspension, and the mixture was shaken in a hydrogen atmosphere at normal pressure for 24 hours. The catalyst was filtered off, and the filtrate was evaporated. The residue, containing 1α,3β,25-tris[(tetrahydro-2H-pyran-2-yl)oxy]-cholest-5-ene, was dissolved in 5 ml of methanol. 10 mg of p-toluenesulphonic acid monohydrate were added. The solution was left at room temperature for 3 hours. While stirring there were added dropwise 5 ml of water, the suspension was suction filtered, and the residue was dried. There was obtained 0.11 g (89%) of 1α,3β,25-trihydroxy-cholest-5-ene which melts at 174°-176° C. after recrystallization from acetone.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additionThe residue, containing 1α,3β,25-tris[(tetrahydro-2H-pyran-2-yl)oxy]-cholest-5-ene
  4. dissolutionwas dissolved in 5 ml of methanol
  5. addition10 mg of p-toluenesulphonic acid monohydrate were added
  6. additionwere added dropwise 5 ml of water
  7. filtrationsuction filtered
  8. customthe residue was dried

Sources & evidence

ORD record
ord-030070e96c64441984f6fac2cf87b014
Source dataset
uspto-grants-1982_01
Patent number
US04312812

Reaction notes

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