HCID 58252548, compound → HCID 58252469, compound

Participants

Reaction Conditions

Reaction Steps

Benzyl 6-bromo-1-tert-butyl-7-hydroxy-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carboxylate (57.9 g, 122 mmol) was dissolved in acetone (1 L) and cooled to 0° C. in an ice bath. To the solution was added Jones Reagent (122 mL) (Fillion, E. Tetrahedron Letters 2004, 46, 1091-1094). The ice bath was removed and the reaction was allowed to warm to room temperature and stir for 45 minutes. Saturated aqueous sodium bicarbonate was added until gas evolution ceased and the pH reached 7. The resulting mixture was filtered through a pad of Celite®, rinsing with ethyl acetate. The filtrate layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed twice with water, once with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated. The residue was crystallized from ethyl acetate/heptanes to afford the title compound (50.4 g, 87%). +ESI (M+H) 474.5; 1H NMR (400 MHz, CDCl3, δ): 7.32 (d, J=9.38 Hz, 6 H), 5.11 (s, 2 H), 4.24 (s, 1 H), 3.58-3.84 (m, 2 H), 3.16-3.41 (m, 2 H), 2.67-2.91 (m, 2 H), 1.80 (br. s., 1 H), 1.61-1.76 (m, 11 H), 1.52-1.61 (m, 1 H).

Provenance & Evidence