Triphenylphosphine → HCID 58664172, compound

HRID 32858Notes

Reaction equation

HRID 32858 reaction equation
[N:1]([CH2:4][CH:5]1[C:9]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])=[CH:8][CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:6]1C(OC(C)(C)C)=O)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:17][C:11]1[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:10]=1[C:9]1[CH:5]([CH2:4][NH2:1])[NH:6][CH:7]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:8]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 71026191(+/-)-tert-Butyl 2-(azidomethyl)-3-(2,5-difluorophenyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Product 1

HCID 58664172HCID 58664172, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-1a (0.21 g, 0.51 mmol) and triphenylphosphine (0.133 g, 0.51 mmol) in THF (10mL) was allowed to stir at rt overnight. The reaction was quenched with water (10 mL) and heated at 60° C. for 1 h. The product was extracted with EtOAc (2×30 mL) and washed with brine (30 mL), dried over MgSO4, filtered and concentrated. The remaining oil was dissolved in CH2CL2 (5 mL)I TFA (2 mL) and allowed to stir at rt overnight. The solvent was removed in vacuo. The remaining oil was dissolved in CH3CN (3 mL) and purified on a Gilson automated system affixed with a YMC J'sphere H80 30×100 mm column (eluting with 5-95% CH3CN +0.1% TFA in water +0.1% TFA over 20 min) to afford pure 2-3a.

Workup

  1. customThe reaction was quenched with water (10 mL)
  2. temperatureheated at 60° C. for 1 h
  3. extractionThe product was extracted with EtOAc (2×30 mL)
  4. washwashed with brine (30 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dissolutionThe remaining oil was dissolved in CH2CL2 (5 mL)I TFA (2 mL)
  9. stirringto stir at rt overnight
  10. customThe solvent was removed in vacuo
  11. dissolutionThe remaining oil was dissolved in CH3CN (3 mL)
  12. custompurified on a Gilson automated system
  13. washaffixed with a YMC J'sphere H80 30×100 mm column (eluting with 5-95% CH3CN +0.1% TFA in water +0.1% TFA over 20 min)
  14. customto afford pure 2-3a

Sources & evidence

ORD record
ord-645d9d5382fd441185ac8f759021cb54
Source dataset
uspto-grants-2008_09
Patent number
US07427637B2

Reaction notes

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