Tetrahydrofuran → (1S)-5-bromo-2,3-dihydro-1H-inden-1-ol

Temperature

35 °C

A round-bottomed flask was charged with 5-bromo-1-indanone (50.0 g, 0.24 mol), anhydrous THF (500 mL) and (R)-methyl-CBS-oxazaborolidine (10.0 g, 0.04 mol) and the solution was heated to 35° C. under N2. Borane-methylsulfide (10.0 M, 650 mL, 6.5 mol) was added dropwise over 1.5 hours. The mixture was stirred at 35° C. for 1 hour. Upon consumption of the starting material (TLC analysis), the reaction was cooled to 0° C. and was quenched with water (200 mL) at such a rate to maintain the reaction temperature below 5° C. The mixture was extracted with EtOAc (4×200 mL). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to give a yellow solid. The solids were dissolved in hot CHCl3 (150 mL) and hexane (300 mL) and upon cooling to room temperature solids precipitated from the solution. After further cooling at 0° C., the solids were collected by vacuum filtration to afford (S)-5-bromo-indan-1-ol (22 g, 44%) as a light-yellow solid. This material was carried on to the next step without further purification.

1. customUpon consumption of the starting material (TLC analysis)
2. temperaturethe reaction was cooled to 0° C.
3. customwas quenched with water (200 mL) at such a rate
4. temperatureto maintain the reaction temperature below 5° C
5. extractionThe mixture was extracted with EtOAc (4×200 mL)
6. washThe combined organic extracts were washed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a yellow solid
11. customprecipitated from the solution
12. temperatureAfter further cooling at 0° C.
13. filtrationthe solids were collected by vacuum filtration

ORD record

ord-d3920ec7ad3441819b35200a6dcf80d7

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609680B2