Potassium bisulfate → HCID 57771527, compound

HRID 2070552Notes

Reaction equation

HRID 2070552 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[C:15](=[O:16])[CH2:14][C:13]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].S([O-])(O)(=O)=O.[K+]>CO>[CH2:1]([O:8][C:9]([CH:11]1[CH:15]([OH:16])[CH2:14][C:13]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 4311764Sodium borohydrideHCID 57771374HCID 57771374, compound

Product 1

HCID 57771527HCID 57771527, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of the crude product (5.23 g) containing 3-oxo-spiro[4.4]nonane-2-carboxylic acid benzyl ester obtained in Step 3 in methanol (100 mL) was added sodium borohydride (254 mg) under ice-cooling, followed by stirring under ice-cooling for 30 minutes. Then, after addition of 10% aqueous potassium hydrogen sulfate solution (10 mL) to the reaction mixture, methanol was evaporated off in vacuo, followed by extraction with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=10:1 to 3:1) to give 3-hydroxy-spiro[4.4]nonane-2-carboxylic acid benzyl ester (less-polar isomer; 1.29 g, more-polar isomer; 2.23 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. customwas evaporated off in vacuo
  4. extractionfollowed by extraction with ethyl acetate
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=10:1 to 3:1)

Sources & evidence

ORD record
ord-90d3b312447f4fb08254e69f73ef2a0b
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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