反应详情

(+/−)-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.

1. waitfor ˜6 hrs
2. customTHF was removed in vacuo
3. additionthe aqueous portion was diluted with 1N HCl (50 mL)
4. extractionextracted 5× with EA (20 mL)
5. customto remove all of triphenylphosphine and triphenylphosphine oxide
6. temperatureThe aq. portion was cooled to ˜5 deg. C
7. additionand adjusted to pH of 10 by dropwise addition of 1N NaOH
8. extractionExtracted with DCM (5×)
9. extractionthe organic extractions
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated
12. customThis material was combined with another similar reaction