Triphenylphosphine → (3RS,4SR)-1-Benzyl-3-(3,4-dichloro-phenyl)-4-[(RS)-1-(4-trifluoromethyl-phenoxy)-ethyl]-pyrrolidine

HRID 906868Notes

Reaction equation

HRID 906868 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:20][C:21]([F:30])([F:29])[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.[CH2:53]([N:60]1[CH2:64][CH:63]([C:65]2[CH:70]=[CH:69][C:68]([Cl:71])=[C:67]([Cl:72])[CH:66]=2)[CH:62]([CH:73](O)[CH3:74])[CH2:61]1)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>C1COCC1>[CH2:53]([N:60]1[CH2:61][CH:62]([CH:73]([O:28][C:25]2[CH:24]=[CH:23][C:22]([C:21]([F:29])([F:30])[F:20])=[CH:27][CH:26]=2)[CH3:74])[CH:63]([C:65]2[CH:70]=[CH:69][C:68]([Cl:71])=[C:67]([Cl:72])[CH:66]=2)[CH2:64]1)[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 5387121Dibenzyl azodicarboxylateHCID 66999712(RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethanol

Product 1

HCID 67131473(3RS,4SR)-1-Benzyl-3-(3,4-dichloro-phenyl)-4-[(RS)-1-(4-trifluoromethyl-phenoxy)-ethyl]-pyrrolidineYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (1.80 g, 5.59 mmol) in THF (40 mL) at 0° C. were added 4-trifluoromethyl-phenol(0.618 g, 3.81 mmol) and then DBAD (0.936 g, 4.07 mmol). After 5 minutes was added (SR)-1-[(3SR,4RS)-1-benzyl-4-(3,4dichloro-phenyl)-pyrrolidin-3-yl]-ethanol (X-B-1) (0.89 g, 2.54 mmol). The reaction mixture was stirred over night at RT, filtered on celite and concentrated under vacuo. Extraction with EtOAc/aq.NaOH 1M, followed by column chromatography (SiO2, EtOAc/H, 1:6) yielded 0.990 g (79%) of the title compound as a colorless oil. ES-MS m/e: 493.0 (M+H+).

Workup

  1. filtrationfiltered on celite
  2. concentrationconcentrated under vacuo
  3. extractionExtraction with EtOAc/aq

Sources & evidence

ORD record
ord-0f4af3cdb3ef4350b9506c2170a2cf70
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

Loading…