Hydrochloric Acid → HCID 57771629, compound

HRID 2070609Notes

Reaction equation

HRID 2070609 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[C:6]1=[O:17])=[O:4].O.O.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl>CO.[Cl-].[Na+].O.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:5]1[CH2:14][C:13]([CH3:15])([CH3:16])[CH2:12][C:7]2([CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]1[OH:17])=[O:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 6093260Calcium chloride, dihydrateHCID 57771483HCID 57771483, compound

Product 1

HCID 57771629HCID 57771629, compoundYield 75.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 9,9-dimethyl-6-oxo-spiro[4.5]decane-7-carboxylic acid methyl ester (450 mg) obtained in Step 1 in methanol (4.5 mL) was added calcium chloride dihydrate (417 mg), followed by stirring under ice-cooling for 15 minutes. Then, to the reaction mixture was added sodium borohydride (90 mg) in three portions, followed by stirring the reaction mixture under ice-cooling for 1.5 hours. To the reaction mixture were added successively 2N aqueous hydrochloric acid solution, toluene and saturated brine, and the mixture was stirred for 5 minutes, followed by separation of the aqueous layer. The organic layer was washed successively with water and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:6) to give 6-hydroxy-9,9-dimethyl-spiro[4.5]decane-7-carboxylic acid methyl ester (341 mg).

Workup

  1. temperaturecooling for 15 minutes
  2. stirringby stirring the reaction mixture under ice-
  3. temperaturecooling for 1.5 hours
  4. stirringthe mixture was stirred for 5 minutes
  5. customfollowed by separation of the aqueous layer
  6. washThe organic layer was washed successively with water and saturated brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:6)

Sources & evidence

ORD record
ord-b83a1c82646c45c68deb8a258501cc7d
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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