Potassium Hydroxide → HCID 59447818, compound

Participants

Reaction Steps

The title compound was prepared according to general procedure B described in connection with Scheme 2. 1-t-Butyl 3-methyl 3-(cyclopropylmethyl)pyrrolidine-1,3-dicarboxylate (1.00 g, 3.5 mmol.) was dissolved in 2 mL MeOH and a solution KOH (0.59 g, 10.6 mmol.) in 2 mL H2O was added. The reaction mixture was microwaved at 130° C. for 30 min. The methanol was evaporated and 10 mL of 10% KHSO4 solution was added to the residue. The acid was extracted with EtOAc (2×20 mL). The combined organic fractions were dried over Na2SO4; evaporation of solvent gave 0.98 g of the desired product as orange oil which crystallized on standing (quantitative yield). 1H NMR (400 MHz, CDCl3): δ 3.81-3.93 (m, 1H), 3.36-3.44 (m, 2H), 2.28 (d, 1H), 2.33-2.46 (m, 1H), 1.83-1.91 (m, 1H), 1.60-1.70 (m, 2H), 1.45 (s, 9H), 0.62-0.75 (m, 1H), 0.42-0.50 (m, 2H), 0.05-0.12 (m, 2H); MS (ESI) m/z: Calculated for C14H23NO4: 269.2. found: 292 (M+Na)+.

Provenance & Evidence