Triphenylphosphine → HCID 69333072, compound

HRID 354402Notes

Reaction equation

HRID 354402 reaction equation
C[C@@:2]1([C:15]([OH:17])=[O:16])[CH2:6][CH:5]([OH:7])[CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH:18]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:37][C:38]1[CH:43]=[C:42]([F:44])[CH:41]=[CH:40][C:39]=1O.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:11]([O:10][C:8]([N:3]1[CH2:4][CH:5]([O:7][C:41]2[CH:40]=[CH:39][C:38]([F:37])=[CH:43][C:42]=2[F:44])[CH2:6][CH:2]1[C:15]([O:17][CH3:18])=[O:16])=[O:9])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1230512,4-DifluorophenolHCID 5363146Diisopropyl azodicarboxylateHCID 69333372Methyl 1-(tert-butoxycarbonyl)-4-hydroxyproline

Product 1

HCID 69333072HCID 69333072, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 1-(tert-butoxycarbonyl)-4-hydroxyproline (4.0 g, 16.3 mmol), Ph3P (5.14 g, 19.6 mmol), and 2,4-difluorophenol (2.55 g, 19.6 mmol) in THF (50 ml) was added DIAD (3.9 ml, 19.6 mmol), and the mixture was heated at reflux for 3 h. After cooling to room temperature, the mixture was concntrated in vacuo and the residue was chromatographed on silica gel with CHCl3-EtOAc (4:1) to give methyl 1-(tert-butoxycarbonyl)-4-(2,4-difluorophenoxy)pyrrolidine-2-carboxylate (5.82 g, quant) as yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. customthe residue was chromatographed on silica gel with CHCl3-EtOAc (4:1)

Sources & evidence

ORD record
ord-97f135f12d1c4067b929bf7f236bf07b
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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