Sodium Hydroxide → 2-(tert-Butoxycarbonyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

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Reaction Conditions

Reaction Steps

A solution of N-t-butoxycarbonyl-5-methoxycarbonylisoindoline (D12) (2.11 g) in MeOH (10 ml) was treated with 1M NaOH and heated at 60° C. for 1 h. The mixture was cooled to rt and the MeOH evaporated. The aqueous was washed with diethyl ether (2×20 ml), then acidified with 5% citric acid solution and extracted with diethyl ether (2×20 ml). The combined extracts were washed with water (2×20 ml), brine (20 ml), dried (MgSO4) and evaporated to give the title compound (D13) (1.47 g). MS electrospray (+ion) 264 (MH+). 1H NMR δ (CDCl3): 8.02 (2H, m), 7.35 (1H, m), 4.75 (2H, s), 4.71 (2H, s), 1.53 (9H, s).

Provenance & Evidence