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

Temperature

0 °C

In situ Preparation of the Compound of Formula (II) wherein R1 is ##STR10## 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. (C) 49 1970] (169 mg, 1 mmol) in THF (70 mL) at ambient temperature and stirred for 16 hrs. α-Tetralone (2.92 g, 19.7 mmol) as a solution in THF (10 mL) was added to the preceding solution over 1 hr, stirred for 15 min after addition was completed, cooled to 0° C., and quenched with methanol (27 mL). After stirring the quenched reaction for 18 hrs, the solvents were removed under vacuum, the residual oil was dissolved in methylene chloride (60 mL), and 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) tetralol 2.89 g (97% yield) 84% ee.

1. stirringstirred for 15 min
2. additionafter addition
3. customquenched with methanol (27 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 (60 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-7bb5823bedee4830bcfce98118759deb

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06005133