Red-Al → (R)-tert-butyl 2-(1'-benzylspiro[indoline-3,4'-piperidine]-4-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

RED-AL (250 μL, 0.83 mmol) was added into a solution of (R)-tert-butyl 2-(1′-benzyl-2-oxospiro[indoline-3,4′-piperidine]-4-yl)pyrrolidine-1-carboxylate (120 mg, 0.26 mmol) in toluene (3 mL), and the resulting solution was heated to 70° C. for 30 minutes. The reaction was quenched by adding EtOAc (5 mL) into the reaction mixture. The resulting mixture was treated with 1M aqueous potassium sodium tartrate (2 mL) and was extracted with EtOAc (10 mL). The organic layer was washed with brine, dried with Na2SO4, filtered and concentrated. The residue was purified with flash chromatography to afford the product (R)-tert-butyl 2-(1′-benzylspiro[indoline-3,4′-piperidine]-4-yl)pyrrolidine-1-carboxylate (50 mg, 43.0%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 7.30-7.40 (m, 4H), 7.18-7.20 (m, 1H), 6.90-7.00 (m, 1H), 6.42-6.52 (m, 1H), 5.20-5.40 (m, 1H), 3.40-3.80 (m, 4H), 3.18-3.40 (m, 1H), 2.80-3.00 (m, 2H), 2.22-2.42 (m, 3H), 2.20 (s, 2H), 1.95-2.02 (m, 2H), 1.70-1.85 (m, 2H), 1.56 (s, 4H), 1.38-1.42 (m, 1H), 1.22-1.30 (m, 1H), 1.20 (s, 6H). MS (APCI+) [M+H]+ 448.

Provenance & Evidence