Water → HCID 59547332, compound

Participants

Reaction Steps

Ester (2S)-di-tert-butyl 4-(aminomethyl)-4-(2-ethoxy-2-oxoethyl)pyrrolidine-1,2-dicarboxylate (C6) (560 mg, 1.45 mmol) was dissolved in THF (12 ml). To this was added 1N lithium hydroxide in water (2.9 ml, 2.9 mmol, 2.0 eq). The mixture was stirred at room temperature overnight. The reaction was cooled to 0° C. and quenched with 1N hydrochloric acid in water. The mixture was blown to dryness with N2 gas and stripped from acetonitrile several times to give 2-((5S)-3-(aminomethyl)-1,5-bis(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acid (D6) (1.45 mmol) as a glassy solid. 1H NMR (DMSO) δ 1.35 (m, 18H), 2.00 (m, 2H), 2.35 (m, 2H), 2.80 (m, 1H), 3.65 (m, 1H), 4.00 (m, 1H); LCMS for C17H30N2O6 358.21 [M], found ES+ 359.21 [M+H]+ and ES− 357.21 [M−H]− at 1.8 minutes retention time, using 10-90% acetonitrile/water (with 0.1% formic acid buffer) gradient over 5 minutes.

Provenance & Evidence