Tempo → HCID 118061571, compound

Participants

Reaction Steps

To a solution of isopropyl 1-(hydroxymethyl)-3,3-dimethoxycyclobutanecarboxylate (2.3 g, 9.90 mmol) in DCM (45 mL) was added iodosobenzene diacetate (4.78 g, 14.85 mmol) and TEMPO (0.155 g, 0.990 mmol) and the mixture was stirred at RT for 8 h. The reaction mass was diluted with DCM (25 mL), washed with and a 10% aq. solution of NaHCO3, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by silica gel chromatography (40 g REDISEP® column, eluting with 5% MeOH in CHCl3). Fractions containing the product were combined and evaporated to afford Intermediate 304A as a pale yellow liquid (1.3 g, 57%). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.62 (s, 1H), 4.96 (s, 1H), 3.04 (d, J=7.18 Hz, 6H), 2.59-2.66 (m, 2H), 2.47 (m, 2H), 1.20 (d, J=6.42 Hz, 6H).

Provenance & Evidence