Triphenylphosphine → 4-(1-Benzhydryl-azetidin-3-yloxy)-1-benzyl-1,3-dihydro-benzoimidazol-2-one

HRID 730563Notes

Reaction equation

HRID 730563 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([OH:17])[C:11]=2[NH:10][C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]([N:32]1[CH2:35][CH:34](O)[CH2:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH:19]([N:32]1[CH2:35][CH:34]([O:17][C:16]2[C:11]3[NH:10][C:9](=[O:18])[N:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:12]=3[CH:13]=[CH:14][CH:15]=2)[CH2:33]1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 578349841-Benzyl-4-hydroxy-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 578349704-(1-Benzhydryl-azetidin-3-yloxy)-1-benzyl-1,3-dihydro-benzoimidazol-2-oneYield 39.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1-benzyl-4-hydroxy-1,3-dihydro-benzoimidazol-2-one (0.104 g., 0.433 mmol) and 1-benzhydryl-azetidin-3-ol (0.114 g., 0.477 mmol) in 0.5 mL anhydrous THF was added triphenyl phosphine (0.125 g., 0.477 mmol) and diisopropyl azodicarboxylate (0.093 mL, 0.477 mmol). The reaction mixture was refluxed for 2 hours, then concentrated in vacuo and purified by preparative TLC (2% methanol in dichloromethane) to give 78 mg (0.17 mmol, 39.5%) of 4-(1-benzhydryl-azetidin-3-yloxy)-1-benzyl-1,3-dihydro-benzoimidazol-2-one as a yellow glass. MS: 462 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. concentrationconcentrated in vacuo
  3. custompurified by preparative TLC (2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-61858fbb72f44d679685665791aec91a
Source dataset
uspto-grants-2009_09
Patent number
US07582760B2

Reaction notes

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