Water → HCID 13686447, compound

HRID 1981877Notes

Reaction equation

HRID 1981877 reaction equation
[C:1]([O:4][C@H:5]1[CH:29]2[C@:24]([CH3:32])([CH2:25][C@@H:26]([F:31])[C:27](=[O:30])[CH2:28]2)[C@@H:23]2[C@H:7]([C@H:8]3[C@:20]([CH3:33])([CH2:21][CH2:22]2)[C@@H:11]([C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]3)[CH2:6]1)(=[O:3])[CH3:2].[BH4-].[Na+].O.C(OCC)(=O)C>C1COCC1.CO>[C:1]([O:4][C@H:5]1[CH:29]2[C@:24]([CH3:32])([CH2:25][C@@H:26]([F:31])[C@@H:27]([OH:30])[CH2:28]2)[C@@H:23]2[C@H:7]([C@H:8]3[C@:20]([CH3:33])([CH2:21][CH2:22]2)[C@@H:11]([C@H:12]([CH3:19])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:10][CH2:9]3)[CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 13686445HCID 13686445, compound

Product 1

HCID 13686447HCID 13686447, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the fluoroketone (3) (270 mg) in THF (24 ml) was added sodium borohydride (90 mg) in methanol (6 ml) at room temperature and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added water and ethyl acetate and the excess reagent was quenched with 2N-HCl. The organic phase was washed with saturated NaHCO3 and brine, and dried over MgSO4. The crude mixture obtained upon evaporation of the solvent was separated by column chromatography on silica gel (10 g). Elution with benzene-ethyl acetate 10:1 gave 6β-acetoxy-2α-fluoro-3α-hydroxycholestane (5) 54 mg, 2%), mp 148°-150° (CHCl3 -MeOH); δ0.79(3H, s, 18-H3), 2.20(3H, s, acetyl), 4.22(1H, m, W1/2 =13 Hz, 3β-H), 4.65(1H, m, 2β-H), and 4.98(1H, m, 6α-H); m/z, 404 (M+ -AcOH), 389,384, 371 and 369.

Workup

  1. customthe excess reagent was quenched with 2N-HCl
  2. washThe organic phase was washed with saturated NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. customThe crude mixture obtained upon evaporation of the solvent
  5. customwas separated by column chromatography on silica gel (10 g)
  6. washElution with benzene-ethyl acetate 10:1

Sources & evidence

ORD record
ord-86c58542a35344cda149d42d331358c2
Source dataset
uspto-grants-1986_06
Patent number
US04594192

Reaction notes

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