Camphoric acid, (-)- → HCID 2750589, compound

HRID 2380935Notes

Reaction equation

HRID 2380935 reaction equation
[C:1](O)(=[O:13])[C@:2]1([CH2:12][CH2:11][C@@H:7]([C:8](O)=[O:9])[C:4]1([CH3:6])[CH3:5])[CH3:3]>C1COCC1.CCOCC>[OH:13][CH2:1][C:2]1([CH3:3])[CH2:12][CH2:11][CH:7]([CH2:8][OH:9])[C:4]1([CH3:6])[CH3:5]

Participants

4

Reactant 1

HCID 219463Camphoric acid, (-)-

Product 1

HCID 2750589HCID 2750589, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1S,3R)-camphoric acid (1) (3.0 g, 14.8 mmol) in dry THF (40 mL) and dry Et2O (30 mL) was added LiALH4 (2.0 g, 52.6 mmol) and the reaction mixture was refluxed for 5 hours. The reaction was then quenched by the addition of Na2SO4.10H2O (8.5 g) and the mixture stirred for 0.5 hour. H2O (100 mL) was added and the aqueous layer extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over anhydrous MgSO4 and the solvents concentrated in vacuo to a residue which was purified over silica (n-hexane/EtOAc, 6:4) to afford 2.39 g (95% yield) of the desired intermediate (2) as crystals which were characterized as follows:

Workup

  1. temperaturethe reaction mixture was refluxed for 5 hours
  2. customThe reaction was then quenched by the addition of Na2SO4.10H2O (8.5 g)
  3. additionH2O (100 mL) was added
  4. extractionthe aqueous layer extracted with CH2Cl2 (3×50 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. concentrationthe solvents concentrated in vacuo to a residue which
  7. customwas purified over silica (n-hexane/EtOAc, 6:4)

Sources & evidence

ORD record
ord-81c4b9984eb44c0098d9f4b8b1592b14
Source dataset
uspto-grants-2012_09
Patent number
US08258126B2

Reaction notes

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