Triphenylphosphine → HCID 67131583, compound

HRID 906878Notes

Reaction equation

HRID 906878 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[N:25][CH:26]=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1.[CH2:50]([N:57]1[CH2:61][C@H:60]([C:62]2[CH:67]=[CH:66][C:65]([F:68])=[C:64]([Cl:69])[CH:63]=2)[C@@H:59]([C@H:70](O)[CH3:71])[CH2:58]1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C1COCC1>[CH2:50]([N:57]1[CH2:61][C@H:60]([C:62]2[CH:67]=[CH:66][C:65]([F:68])=[C:64]([Cl:69])[CH:63]=2)[C@@H:59]([C@@H:70]([O:27][C:24]2[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][N:25]=2)[CH3:71])[CH2:58]1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 67131696HCID 67131696, compoundHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 67131583HCID 67131583, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (141 mg, 0.53 mmol) in THF (8 mL) at 0° C. were added 5-chloro-pyridin-2-ol (47 mg, 0.36 mmol) and then DBAD (90 mg, 0.39 mmol). After 5 minutes was added (R)-1-[(3R,4S)-1-benzyl-4-(3-chloro-4-fluoro-phenyl)-pyrrolidin-3-yl]-ethanol (81 mg, 0.24 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, 1:3) yielded 88 mg (81%) of the title compound as a colorless oil. ES-MS m/e: 446.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-8f364cfba28647589521040f13731ad1
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

Loading…