Water → HCID 86735823, compound

HRID 866340Notes

Reaction equation

HRID 866340 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].O>O1CCCC1>[O:3]1[C@H:5]2[CH:6]([OH: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]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22803980HCID 22803980, compound

Product 1

HCID 86735823HCID 86735823, compound

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. Water was cautiously added to the reaction mixture cooled in an ice bath. The mixture was stirred for about 10 minutes and then evaporated at a bath temperature of 35° C in vacuo. The residue was partitioned between methylene chloride and water (ca. 1:1) and the organic layer was separated. The organic phase was washed with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate and filtered. Evaporation of the filtrate gave 1α,2α-epoxy-25-hydroxy-6β-methylsulfonyloxy-5α-cholestan-3-ol, as a white foam.

Workup

  1. temperaturecooled in an ice bath
  2. additionAfter the addition
  3. temperaturecooled in an ice bath
  4. stirringThe mixture was stirred for about 10 minutes
  5. customevaporated at a bath temperature of 35° C in vacuo
  6. customThe residue was partitioned between methylene chloride and water (ca. 1:1)
  7. customthe organic layer was separated
  8. washThe organic phase was washed with water, saturated sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-50078bb7c53747ed988abd8d77805e2a
Source dataset
uspto-grants-1978_07
Patent number
US04098801

Reaction notes

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