Sodium borohydride → HCID 57050928, compound

HRID 863172Notes

Reaction equation

HRID 863172 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][CH2:6][C@@H:5]([C:8]([CH3:10])=[CH2:9])[C@H:4]([C:11]([O:13][CH3:14])=[O:12])[C:3]1=[O:15].O.O.O.O.O.O.O.[Cl-].[Ce+2].[Cl-].[BH4-].[Na+]>CO.C(OCC)(=O)C>[OH:15][C@H:3]1[C:2]([CH3:16])([CH3:1])[CH2:7][CH2:6][C@@H:5]([C:8]([CH3:10])=[CH2:9])[C@@H:4]1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 57102460HCID 57102460, compoundHCID 178526981HCID 178526981, compound

Product 1

HCID 57050928HCID 57050928, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl (1S,6R)-3,3-dimethyl-6-(1-methylvinyl)-2-oxocyclohexane-1-carboxylate (1.38 g) and cerium (II) chloride heptahydrate (2.14 g) in methanol (10 ml) was added sodium borohydride (217 mg) at 0° C. The mixture was stirred at room temperature for 1 hr, and the reaction was quenched by addition of water. The pH of the mixture was adjusted to pH 7 with 0.1N hydrochloric acid. The mixture was extracted with ether. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Purification of the residue by flash column chromatography (using n-hexane:ethyl acetate=20:1 as an eluent) gave methyl (1S,2R,6R)-2-hydroxy-3,3-dimethyl-6-(1-methylvinyl)cyclohexane-1-carboxylate (1.15 g, 83% yield).

Workup

  1. customthe reaction was quenched by addition of water
  2. extractionThe mixture was extracted with ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash column chromatography (

Sources & evidence

ORD record
ord-4c1684f3a0c64436a4a372b34a6e16d3
Source dataset
uspto-grants-1998_02
Patent number
US05719291

Reaction notes

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