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

Participants

Reaction Steps

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:

Provenance & Evidence