Tetrahydrofuran → HCID 58367211, compound

Temperature

-78 °C

To a stirred suspension of crude (S,E)-N-(4-bromo-2,3-dihydro-1H-inden-1-ylidene)-2-methylpropane-2-sulfinamide IND INT-9 in toluene (250 mL) under N2 was added anhydrous THF (250 mL) and the reaction mixture was cooled to −78° C. Sodium borohydride (26.8 g, 710 mmol) was added in four portions over 30 min (internal temperature maintained below −65° C.). The reaction mixture was stirred at −78° C. for 30 min before it was warmed to room temperature over 1 h and continued to stir for additional 1 h. The reaction mixture was filtered through Celite pad to remove Ti salts. The filtrate was treated with EA (500 mL), saturated sodium potassium tartrate (200 mL), and brine (50 mL) and the mixture stirred at room temperature overnight. The mixture was filtered through a celite pad and the filtrate dried over MgSO4. The crude product was obtained by concentration to dryness gave 46 g (61%) of (S)-N-((S)-4-bromo-2,3-dihydro-1H-inden-1-yl)-2-methylpropane-2-sulfinamide IND INT-11 as an off-white solid which was used in the next experiment without purification. LCMS-ESI (m/z) calculated C13H16BrNOS: 313.0; found 314.0 [M+H]+, tR=3.84 min.

1. temperature(internal temperature maintained below −65° C.)
2. temperaturewas warmed to room temperature over 1 h
3. stirringto stir for additional 1 h
4. filtrationThe reaction mixture was filtered through Celite pad
5. customto remove Ti salts
6. additionThe filtrate was treated with EA (500 mL), saturated sodium potassium tartrate (200 mL), and brine (50 mL)
7. stirringthe mixture stirred at room temperature overnight
8. filtrationThe mixture was filtered through a celite pad
9. dry with materialthe filtrate dried over MgSO4
10. customThe crude product was obtained by concentration to dryness

ORD record

ord-1fe08012b4fa4119aaf5547943734d2c

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507538B2