Triphenylphosphine → HCID 86588701, compound

HRID 887625Notes

Reaction equation

HRID 887625 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][CH:7]=1.[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[CH2:30]O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH:26]1[CH2:30][O:17][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=1)([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 550865tert-Butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 5462977Diethyl azodicarboxylateHCID 133206092-(3-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86588701HCID 86588701, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(3-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.30 g), 2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.04 g), PPh3 (2.64 g) and molecular sieves 4 Å in THF (100 mL) was added DEAD (1.55 mL) slowly. The reaction was stirred at RT for 4 h and at reflux overnight. After filtration to remove solids, the filtrate was concentrated and the residue was taken up into Et2O. The organic phase was washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and evaporated to give a viscous brown oil, which was purified by chromatography through silica gel (500 g, 30% to 50% EtOAc in hexanes) to afford 2-[1-(3-amino-phenyl)-2,2,2-trifluoro-1-trifluoromethyl-ethoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown oil.

Workup

  1. temperatureat reflux overnight
  2. filtrationAfter filtration
  3. customto remove solids
  4. concentrationthe filtrate was concentrated
  5. washThe organic phase was washed with saturated NaHCO3 and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customto give a viscous brown oil, which
  9. customwas purified by chromatography through silica gel (500 g, 30% to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e70d389a946a4a78920f8567b415087c
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

Loading…