Water → HCID 68350312, compound

Participants

Reaction Steps

(+/−)-Cis-benzyl 3-azido-4-methoxypyrrolidine-1-carboxylate (5.43 g, 19.65 mmol) was dissolved in THF (50 mL) and added triphenylphosphine (5.41 g, 20.64 mmol) and stirred at RT overnight. Added water (6 mL) and warmed to 60 deg. C. for ˜6 hrs. THF was removed in vacuo and the aqueous portion was diluted with 1N HCl (50 mL) and extracted 5× with EA (20 mL) to remove all of triphenylphosphine and triphenylphosphine oxide. The aq. portion was cooled to ˜5 deg. C. and adjusted to pH of 10 by dropwise addition of 1N NaOH. Extracted with DCM (5×) and the organic extractions were combined, dried (Na2SO4) and concentrated. This material was combined with another similar reaction performed on 22.8 mmol scale to afford a total of 8.0 g (75%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.36 (5 H, m), 5.34 (2 H, m), 3.45-3.73 (5 H, m), 3.42 (3 H, s), 3.13-3.22 (1 H, d, m), 1.28-1.31 (2 H, br s). LCMS: M+1=251, Rt=1.54 min.

Provenance & Evidence