Water → HCID 86735822, compound

HRID 866342Notes

Reaction equation

HRID 866342 reaction equation
[BH4-].[Na+].[O:3]1[C@H:5]2[C:6](=[O:37])[CH2:7][C@H:8]3[C@:29]([CH3:30])([C@@H:4]12)[C@@H:28]1[C@H:11]([C@H:12]2[C@:25]([CH3:31])([CH2:26][CH2:27]1)[C@@H:15]([C@H:16]([CH3:24])[CH2:17][CH2:18][CH2:19][C:20]([OH:23])([CH3:22])[CH3:21])[CH2:14][CH2:13]2)[CH2:10][C@H:9]3[O:32][S:33]([CH3:36])(=[O:35])=[O:34].[BH4-].[Li+].O>O1CCCC1>[OH:3][C@@H:4]1[C@@:29]2([CH3:30])[C@@H:8]([C@H:9]([O:32][S:33]([CH3:36])(=[O:35])=[O:34])[CH2:10][C@@H:11]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:31])[C@H:12]3[CH2:13][CH2:14][C@@H:15]2[C@H:16]([CH3:24])[CH2:17][CH2:18][CH2:19][C:20]([OH:23])([CH3:22])[CH3:21])[CH2:7][CH:6]([OH:37])[CH2:5]1

Participants

6

Reactant 4

HCID 962Water2×HCID 4148881Lithium borohydrideHCID 4311764Sodium borohydrideHCID 22803980HCID 22803980, compound

Product 1

HCID 86735822HCID 86735822, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-molar diborane-tetrahydrofuran complex (not stabilized with sodium borohydride, 157 ml) cooled in an ice bath, was added dropwise over about 25 minutes a solution of 1α,2α-epoxy-6β-methylsulfonyloxy-5α-cholestan-25-ol-3-one (20.0 g, 0.392 mole), in tetrahydrofuran (100 ml) with stirring under an atmosphere of nitrogen. After the addition was complete, the solution was stirred for about 25 minutes. Lithium borohydride (3.40 g, 0.155 mole) was added in 1 portion to the reaction mixture, with stirring. The suspension was stirred in an ice bath for about 6 hours and then stored in a refrigerator (ca. 3° 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. temperaturecooled in an ice bath
  2. additionAfter the addition
  3. stirringwith stirring
  4. stirringThe suspension was stirred in an ice bath for about 6 hours
  5. customstored in a refrigerator (ca. 3° C) overnight
  6. temperaturecooled in an ice bath
  7. extractionthe solution was extracted with methylene chloride
  8. customThe layers were separated
  9. washthe organic phase was washed successively with water and saturated sodium chloride solution
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-ce9c445036064cb69430af9d466a9028
Source dataset
uspto-grants-1978_07
Patent number
US04098801

Reaction notes

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