Reaction #2031604
Related Literature (1)
openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US06329390B1
Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of (S)-5-bromo-3-[(N-methylpyrrolidin-2-yl)methyl]-l H-indole (Example 3c, 1.00 g, 3.41 mmol) in THF (15 mL) under argon, was added sodium hexamethyldisilazide (6.82 mL, 6.82 mmol and the resulting solution was stirred at room temperature for 20 min. The reaction mixture was cooled to 0° C. and to this was added a solution of t-butydimethylsilyl chloride (1.03 g, 6.82 mmol) in THF (4 mL) and the resulting culture was warmed to room temperature and stirred for 1 hour. The solvent as removed in vacuo and the resulting product was diluted with water (10 mL) and extracted with ethyl acetate (2×10 mL). The ethyl acetate extract was washed with brine (10 mL), dried (Na2SO4), filtered and the filtrate was evaporated to dryness. The crude residue was subjected to flash silica gel chromography to afford the title compound as a yellow oil (1.07 g, 79%). 13C NMR (CDCl3)δ: 140.1, 133.1, 129.8, 124.1, 121.5, 115.8, 115.2, 112.7, 66.2, 7.6, 40.9, 31.6, 30.1, 26.2, 21.9, 19.5, −3.96 The reaction mixture was cooled to 0° C. the resulting culture was warmed to room temperature stirred for 1 hour The solvent as removed in vacuo the resulting product was diluted with water (10 mL) extracted with ethyl acetate (2×10 mL) The ethyl acetate extract was washed with brine (10 mL) dried (Na2SO4) filtered the filtrate was evaporated to dryness
Source ID: ord-c0ced1bf0ae943769994578b186ea2c8