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

Temperature

0 °C

Borane methylsulfide complex (neat, ~10M, 0.44 mL, 4.4 mmol) was added to a solution of (1R, 2S)-2-tert-butyl-2-aminophenylethanol [Angew. Chem. Int. Ed. Engl. 26 1141 (1987)] (120 mg, 0.62 mmol) in THF (22 mL) at ambient temperature and stirred for 16 hrs. α-Tetralone (906 mg, 6.2 mmol) as a solution in THF (3 mL) was added to the preceding solution over a 1 hr, stirred for 15 min after addition was completed, cooled to 0° C., and quenched with methanol (20 mL). After stirring the quenched reaction for 18 hrs, the solvents were removed under vacuum, the residual oil was dissolved in methylene chloride (30 mL), washed with pH 4 phosphate buffer (30 mL), water (30 mL), treated with magnesium sulfate, and the solvent was removed under vacuum to give the (R) tetralol 841 mg (91% yield) 82% ee.

1. stirringstirred for 15 min
2. additionafter addition
3. customquenched with methanol (20 mL)
4. stirringAfter stirring
5. customthe quenched reaction for 18 hrs
6. customthe solvents were removed under vacuum
7. dissolutionthe residual oil was dissolved in methylene chloride (30 mL)
8. washwashed with pH 4 phosphate buffer (30 mL), water (30 mL)
9. additiontreated with magnesium sulfate
10. customthe solvent was removed under vacuum

ORD record

ord-579d8f36b8e64514b3178a7d52565126

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06037505