Triphenylphosphine → HCID 67131717, compound

HRID 906901Notes

Reaction equation

HRID 906901 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])=[CH:64][CH:63]=2)[C@@H:59]([C@H:69](O)[CH3:70])[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:63]=[CH:64][C:65]([F:68])=[CH:66][CH:67]=2)[C@@H:59]([C@@H:69]([O:27][C:24]2[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][N:25]=2)[CH3:70])[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 67131561HCID 67131561, compoundHCID 1785160645-chloropyridin-2-ol

Product 1

HCID 67131717HCID 67131717, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of PPh3 (PPh3 polymer bound, 3 mmol PPh3/g resin) (0.36 g, 1.1 mmol) in THF (40 mL) at 0° C. were added 5-chloro-pyridin-2-ol (97 mg, 0.75 mmol) and then DBAD (0.18 g, 0.80 mmol). After 5 minutes was added (R)-1-[(3R,4S)-1-benzyl-4-(4-fluoro-phenyl)-pyrrolidin-3-yl]-ethanol (0.15 g, 0.50 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 0.15 g (73%) of the title compound as a colorless oil. ES-MS m/e: 411.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-a47959af166f4ec79fa8722facd4b034
Source dataset
uspto-grants-2011_09
Patent number
US08012998B2

Reaction notes

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