Water → HCID 68350312, compound

HRID 877713Notes

Reaction equation

HRID 877713 reaction equation
[N:1]([C@H:4]1[C@@H:8]([O:9][CH3:10])[CH2:7][N:6]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][C@H:4]1[C@@H:8]([O:9][CH3:10])[CH2:7][N:6]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 92019678HCID 92019678, compound

Product 1

HCID 68350312HCID 68350312, compoundYield 162.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(+/−)-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.

Workup

  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

Sources & evidence

ORD record
ord-7a5142abcc3d47babee4939c9fd4a27d
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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