Triphenylphosphine → 1-[(1R)-3-chloro-1-phenylpropyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one

HRID 2246744Notes

Reaction equation

HRID 2246744 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[NH:5][C:4]1=[O:12])[CH3:2].[Cl:13][CH2:14][CH2:15][C@@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:13][CH2:14][CH2:15][C@@H:16]([N:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N:3]([CH2:1][CH3:2])[C:4]1=[O:12])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 823201-EbioHCID 2777894(S)-(-)-3-Chloro-1-phenyl-1-propanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 685251621-[(1R)-3-chloro-1-phenylpropyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-oneYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-ethyl-1,3-dihydro-benzimidazol-2-one (1 g, 6.2 mmol), (S)-(−)-3-chloro-1-phenyl-1-propanol (1.16 g, 6.8 mmol), and triphenylphosphine (1.78 g, 6.8 mmol) in anhydrous THF (25 mL) was added DIAD (1.38 g, 6.8 mmol) under nitrogen at room temperature. The mixture was stirred under nitrogen at room temperature for 18 hrs and solvent removed in vacuo. The residue was purified by a silica gel column (33% ethyl acetate in hexane) to afford 1-[(1R)-3-chloro-1-phenylpropyl]-3-ethyl-1,3-dihydro-2H-benzimidazol-2-one as an oil (0.5g, 26%). MS (ESI) m/z 315.

Workup

  1. customsolvent removed in vacuo
  2. customThe residue was purified by a silica gel column (33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-98e134f502f542fb950ab95a001add18
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

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