Water → HCID 86735822, compound

HRID 866341Notes

Reaction equation

HRID 866341 reaction equation
[BH4-].[Na+].[BH4-].[Li+].[O:5]1[C@H:7]2[CH:8]([OH:39])[CH2:9][C@H:10]3[C@:31]([CH3:32])([C@@H:6]12)[C@@H:30]1[C@H:13]([C@H:14]2[C@:27]([CH3:33])([CH2:28][CH2:29]1)[C@@H:17]([C@H:18]([CH3:26])[CH2:19][CH2:20][CH2:21][C:22]([OH:25])([CH3:24])[CH3:23])[CH2:16][CH2:15]2)[CH2:12][C@H:11]3[O:34][S:35]([CH3:38])(=[O:37])=[O:36].O>O1CCCC1>[OH:5][C@@H:6]1[C@@:31]2([CH3:32])[C@@H:10]([C@H:11]([O:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH2:12][C@@H:13]3[C@@H:30]2[CH2:29][CH2:28][C@@:27]2([CH3:33])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[C@H:18]([CH3:26])[CH2:19][CH2:20][CH2:21][C:22]([OH:25])([CH3:24])[CH3:23])[CH2:9][CH:8]([OH:39])[CH2:7]1

Participants

6

Reactant 4

HCID 962Water2×HCID 4148881Lithium borohydrideHCID 4311764Sodium borohydrideHCID 86735823HCID 86735823, compound

Product 1

HCID 86735822HCID 86735822, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-molar diborane-tetrahydrofuran complex (not stabilized with sodium borohydride, 157 ml) and lithium borohydride (3.4 g, 0.155 mole) cooled in an ice bath was added dropwise over about 25 minutes a solution of 1α,2α-epoxy-25-hydroxy-6β-methylsulfonyloxy-5α-cholestan-3-ol (20.0 g, 0.392 mole) in tetrahydrofuran (100 ml) with stirring under nitrogen. The suspension was stirred at 0° for about 6 hours, and then stored in a refrigerator (ca. 30° C) overnight. Water (200 ml) was added cautiously to the reaction mixture cooled in an ice bath. An additional 200 ml of water was added to the turbid solution and the solution was extracted with methylene chloride. The layers were separated and the organic phase was washed successively with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate gave 22 g of 1α,25-dihydroxy-6β-methylsulfonyloxy-5α-cholestan-3-ol as a white foam.

Workup

  1. additionTo a mixture of 1-molar diborane-tetrahydrofuran complex (not
  2. temperaturecooled in an ice bath
  3. stirringThe suspension was stirred at 0° for about 6 hours
  4. customstored in a refrigerator (ca. 30° C) overnight
  5. temperaturecooled in an ice bath
  6. extractionthe solution was extracted with methylene chloride
  7. customThe layers were separated
  8. washthe organic phase was washed successively with water and saturated sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-4d75541ac9334975ad8f7d3a23b2b204
Source dataset
uspto-grants-1978_07
Patent number
US04098801

Reaction notes

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