N-bromobutanimide → HCID 70654455, compound

Participants

Reaction Steps

Benzyl 2-tert-butyl-2,4-dihydrospiro[indazole-5,4′-piperidine]-1′-carboxylate (560 mg, 1.48 mmol) was dissolved in a 20% methanol/tetrahydrofuran mixture (25 mL). N-bromosuccinimide (315 mg, 1.77 mmol) was added and the mixture was stirred for 30 minutes. The mixture was concentrated under reduced pressure. The resultant oil was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was dried over sodium sulfate, filtered and concentrated. The resultant oil was purified by flash column chromatography (10-80% ethyl acetate/heptane) to yield 538 mg (73%) of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3, δ): 7.27-7.43 (m, 6 H), 5.12 (s, 2 H), 4.74 (d, J=2.7 Hz, 1 H), 4.41 (d, J=2.5 Hz, 1 H), 3.60-3.84 (m, 2 H), 3.54-3.61 (m, 3 H), 3.14-3.39 (m, 2 H), 2.59 (s, 2 H), 1.86 (br. s., 1 H), 1.69 (br. s., 3 H), 1.51-1.60 (m, 9 H).

Provenance & Evidence