反应详情

温度

-10 °C

Preparation 5(S)-Hydroxy-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester: To an oven-dried 2 L round-bottomed flask equipped with an argon inlet/outlet and magnetic stirring was added (R)-2-methyl-CBS-oxazaborolidine (7.4 mL of a 1M soln in toluene, 7.4 mmol, Aldrich). Toluene 190 mL was added and the reaction was cooled in an ice-salt bath (bath temp. =−10° C.). BH3—SMe2 was added (17 mL, 180 mmol, Aldrich), then 5-oxo-5,6,7,8-tetrahydro-naphth-alene-2-carboxylic acid methyl ester (30 g, 150 mmol, Albany Molecular) in 200 mL of THF was added over 5 h using a syringe pump. After the addition was complete, the mixture was stirred for an additional 1 h. The mixture was poured into an addition funnel, and the mixture was added to 200 mL of MeOH, cooled in a ice-salt bath, over 30 min at such a rate that the internal temp. was kept below 0° C. The mixture was concentrated in vacuo. Et2O (1 L) was added, and the mixture was washed with 1M H3PO4 (3×), satd NaHCO3, and brine (ca. 400 mL each wash). The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in Et2O again (500 mL), and the mixture was washed with 1M H3PO4 (3×200 mL), satd NaHCO3, and brine. After drying the organic layer over MgSO4, the mixture was filtered and concentrated in vacuo, which gave the title compound as a white-yellow solid. MS (+ion ESI) m/z=207 (MH+), 189 (MH+—H2O).

1. customTo an oven-dried 2 L round-bottomed flask equipped with an argon inlet/outlet
2. additionAfter the addition
3. stirringthe mixture was stirred for an additional 1 h
4. additionThe mixture was poured into an addition funnel
5. temperaturecooled in a ice-salt bath, over 30 min at such a rate that the internal temp
6. customwas kept below 0° C
7. concentrationThe mixture was concentrated in vacuo
8. additionEt2O (1 L) was added
9. washthe mixture was washed with 1M H3PO4 (3×), satd NaHCO3, and brine (ca. 400 mL each wash)
10. dry with materialThe organic layer was dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. dissolutionThe residue was dissolved in Et2O again (500 mL)
14. washthe mixture was washed with 1M H3PO4 (3×200 mL), satd NaHCO3, and brine
15. dry with materialAfter drying the organic layer over MgSO4
16. filtrationthe mixture was filtered
17. concentrationconcentrated in vacuo, which