1-Tetralone → (R)-(-)-1,2,3,4-Tetrahydro-1-naphthol

Temperature

0 °C

Borane dimethylsulfide complex (2M in THF, 7.0 mL, 0.014 moles) was added over 45 minutes at ambient temperature to a solution of α-tetralone (2.92 g, 0.02 moles) and the title compound of Example 1 (247 mg, 0.001 moles) in THF (80 mL). The reaction mixture was stirred for 15 minutes (at which time thin layer chromatography indicated complete consumption of α-tetralone) and then cooled to 0° C. and quenched with methanol 27 mL). The quenched solution was allowed to warm to ambient temperature, with stirring, for 16 hours. The solvents were removed in vacuo and the residue was redissolved with methylene chloride (50 mL) and pH4 phosphate buffer (50 mL). The phases were separated and the organic phase was washed with water (50 mL), treated with MgSO4 and filtered. The solvent was removed in vacuo to afford 2.93 (99%) of -(R)-(+)-1,2,3,4-tetrahydro-1-naphthol as a white solid. HPLC with a chiral support demonstrated that the product had a 94% e.e.

1. custom(at which time thin layer chromatography indicated complete consumption of α-tetralone)
2. customquenched with methanol 27 mL)
3. temperatureto warm to ambient temperature
4. stirringwith stirring, for 16 hours
5. customThe solvents were removed in vacuo
6. dissolutionthe residue was redissolved with methylene chloride (50 mL) and pH4 phosphate buffer (50 mL)
7. customThe phases were separated
8. washthe organic phase was washed with water (50 mL)
9. additiontreated with MgSO4
10. filtrationfiltered
11. customThe solvent was removed in vacuo

ORD record

ord-85dbacfe1dec4614b4ce2abc9b7ca5df

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05552548