Lithium borohydride → HCID 28065545, compound

Temperature

50 °C

To a solution of methyl 3-{[(1R)-1-methylpropyl]oxy}benzoate (3.50 g, 16.8 mmol) in THF (67 mL) was added 2M lithium borohydride solution in THF (25.2 ml, 50.4 mmol). The reaction was heated to 50° C. overnight. The reaction was quenched with MeOH and the solvents were concentrated. The residue was dissolved in EtOAc and washed with saturated NaHCO3. The aqueous phase was extracted with dichloromethane and the organics were combined, washed with H2O (2 times) dried with MgSO4, filtered, and concentrated. The residue was purified on a silica gel cartridge (10% EtOAc/hexanes to 20% EtOAc/hexanes) to give the desired product.

1. customThe reaction was quenched with MeOH
2. concentrationthe solvents were concentrated
3. dissolutionThe residue was dissolved in EtOAc
4. washwashed with saturated NaHCO3
5. extractionThe aqueous phase was extracted with dichloromethane
6. washwashed with H2O (2 times)
7. dry with materialdried with MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified on a silica gel cartridge (10% EtOAc/hexanes to 20% EtOAc/hexanes)

ORD record

ord-e7da34c2905843038d2ee24a4cf323ac

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211904B2