Sodium Bicarbonate → HCID 131731867, compound

HRID 75061Notes

Reaction equation

HRID 75061 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C@@H:9]([CH:10]=[O:11])[CH2:8][C@H:7]2[CH2:12][C@@H:5]1[C:6]2([CH3:14])[CH3:13].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[CH3:1][O:2][N:3]=[C:4]1[C@@H:9]([CH2:10][OH:11])[CH2:8][C@H:7]2[CH2:12][C@@H:5]1[C:6]2([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86667459(1R,3S,5R)-2-(methoxyimino)-6,6-dimethylbicyclo[3.1.1]heptane-3-carbaldehyde2×

Product 1

HCID 131731867HCID 131731867, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1R,3S,5R)-2-(methoxyimino)-6,6-dimethylbicyclo[3.1.1]heptane-3-carbaldehyde, 77b, (0.70 g, 3.58 mmol) in methanol (15 mL) was added sodium borohydride (0.16 g, 4.30 mmol). After stirring at room temperature for 30 minutes, the reaction was diluted into aqueous saturated NaHCO3 solution and extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified via silica gel chromatography (0-50% EtOAc/Hexanes gradient) to afford 330 mg of the desired alcohol as mixture of oxime isomers.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified via silica gel chromatography (0-50% EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-cd6d3508e65846baae0ce7abd995aa57
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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