Methanol → HCID 12966955, compound

HRID 2229470Notes

Reaction equation

HRID 2229470 reaction equation
[O:1]=[C:2]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])/[CH:3]=[CH:4]/[C@H:5]1[C@H:12]([O:13][C:14](=[O:27])[C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:17][CH:16]=2)[CH2:11][C@H:10]2[C@@H:6]1[CH2:7][C:8](=[O:28])[O:9]2.CO.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>C1COCC1>[OH:1][C@@H:2]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])/[CH:3]=[CH:4]/[C@H:5]1[C@H:12]([O:13][C:14](=[O:27])[C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:19][CH:20]=2)[CH2:11][C@H:10]2[C@@H:6]1[CH2:7][C:8](=[O:28])[O:9]2

Participants

6

Reactant 4

HCID 887MethanolHCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 15003065HCID 15003065, compound

Product 1

HCID 12966955HCID 12966955, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The unsaturated ketone (3) (3.03 g) was dissolved into a mixed solvent of methanol (60 ml) and THF (7 ml). Into the obtained solution cerium (III) chloride.7H2O (2.38 g) was added at −20° C., and stirred at the same temperature for 10 minutes, into which sodium borohydride (0.25 g) was added and stirred for 5 minutes. A crude compound obtained by a usual work-up was purified using a column chromatography to give the title compound (4a) as a compound having a lower polarity and the 3R-hydroxy compound (4b) of the title compound (4a) as a compound having a higher polarity. Yield: 4.58 9 (4a:3S-hydroxy compound)

Workup

  1. addition7H2O (2.38 g) was added at −20° C.
  2. additionwas added
  3. customA crude compound obtained by a usual work-up
  4. customwas purified

Sources & evidence

ORD record
ord-4dbc69e487e340848990e7273ffe053e
Source dataset
uspto-grants-2002_07
Patent number
US06420422B1

Reaction notes

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