Triphenylphosphine → HCID 86614210, compound

HRID 888090Notes

Reaction equation

HRID 888090 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][C@H: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][C@H: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 643448(S)-(-)-N-Boc-prolinolHCID 5462977Diethyl azodicarboxylateHCID 133206092-(3-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86614210HCID 86614210, 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), (S)-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 for overnight. After filtration to remove solids, the filtrate was concentrated and the residue was taken into Et2O. The organic phase was washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and evaporated to give a crude compound as very viscous brown oil, which was purified by chromatography through silica gel (500 g, 30% to 50% EtOAc in hexanes) to afford (S)-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 for 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 crude compound as very 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-fc99ffb73d7742f98234fecb34d9455b
Source dataset
uspto-grants-2012_08
Patent number
US08247556B2

Reaction notes

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