Methylamine → Tert-butyl 3-(methylcarbamoyl)spiro[indene-1,4'-piperidine]-1'-carboxylate

Participants

Reaction Steps

A solution of methylamine in THF (2 mL) was added to a stirred solution of 1′-(tert-butyoxycarbonyl)spiro[indene-1,4′-piperidine]-3-carboxylic acid (C4) (0.51 g, 1.55 mmol), EDAC HCl (0.6 g, 3.00 mmol), HOBt (0.31 g ) in DMF (10 mL), and the solution was stirred at room temperature for 12 h. The solution was poured into water (50 mL), the aqueous layer was extracted with EtOAc (3×50 mL), dried, and concentrated under reduced pressure. The crude product was purified by Biotage SP1 on silica gel eluting with 12-100% EtOAc in hexanes to provide tert-butyl 3-(methylcarbamoyl)spiro[indene-1,4′-piperidine]-1′-carboxylate (C5) as a white solid (0.45 g). LC/MS (10-90% over 3 min with 0.9% FA) m/z 343 (M+1), Rt 3.0 minutes. 1HNMR (500 mHz, CDCl3) δ 7.73 (d, 1H), 7.23 (m, 3H), 7.14 (s, 1H), 6.05 (brm, 1H), 4.11 (m, 2H), 3.03 (m, 2H), 2.93 (d, 3H), 1.95 (m, 2H), 1.44 (s, 9H), 1.30 (m, 2H).

Provenance & Evidence