Sodium borohydride → HCID 24271770, compound

HRID 72139Notes

Reaction equation

HRID 72139 reaction equation
[O:1]=[C:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][CH:5]([C:11]([O:13][CH3:14])=[O:12])[CH2:6]2.[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][CH:5]([C:11]([O:13][CH3:14])=[O:12])[CH2:6]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19245419Methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate

Product 1

HCID 24271770HCID 24271770, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 9-oxobicyclo[3.3.1]nonane-3-carboxylate (190 mg, 0.97 mmol) in methanol was added NaBH4 (76 mg, 2 mmol) at 0° C. The mixture was stirred at rt for 2 h, and concentrated. The residue was diluted with water, and the mixture was extracted with Et2O. The organic layer was concentrated to give methyl 9-hydroxybicyclo-[3.3.1]nonane-3-carboxylate, which was used in the next step directly without purification (140 mg, crude).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with water
  3. extractionthe mixture was extracted with Et2O
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-dce7bc7d006743a7bc612f2893988bea
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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