Acetophenone → 1,2,3,4-Tetrahydro-2-naphthalenol

Temperature

0 °C

In situ Preparation of the Compound of Formula (II) wherein R1 is ##STR11## Borane methylsulfide complex (neat, ~10M, 1.4 mL, 14 mmol) was added to a solution of cis, exo-3-amino-2-hydroxybornane [J. Chem. Soc. 49, 1970] (169 mg, 1 mmol) in THF (70 mL) at ambient temperature and was stirred for 16 hours. Acetophenone (2.36 g, 24.6 mmol) as a solution in THF (10 mL) was added to the preceding solution over one hour, stirred for fifteen minutes after addition was completed, cooled to 0° C., and quenched with methanol (27 mL). After stirring the quenched reaction for 18 hours, the solvents were removed under vacuum, the residual oil was dissolved in methylene chloride (50 mL), washed with pH 4 phosphate buffer (50 mL), water (50 mL), treated with magnesium sulfate, and the solvent was removed under vacuum to give the (R) phenethyl alcohol. 2.17 g (92% yield) 88% ee.

1. stirringstirred for fifteen minutes
2. additionafter addition
3. customquenched with methanol (27 mL)
4. stirringAfter stirring
5. customthe quenched reaction for 18 hours
6. customthe solvents were removed under vacuum
7. dissolutionthe residual oil was dissolved in methylene chloride (50 mL)
8. washwashed with pH 4 phosphate buffer (50 mL), water (50 mL)
9. additiontreated with magnesium sulfate
10. customthe solvent was removed under vacuum

ORD record

ord-c22203a73d374481b8d0be7b73943ac9

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06005133