(Isocyanatomethylene)dibenzene → (R)-3-Benzhydryl-1-(1-benzyl-pyrrolidin-3-yl)-1-methyl-urea

HRID 1786540Notes

Reaction equation

HRID 1786540 reaction equation
[C:1]([N:9]1[CH2:13][CH2:12][C@@H:11]([NH:14][CH3:15])[CH2:10]1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1([CH:22]([N:29]=[C:30]=[O:31])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[CH:22]([NH:29][C:30](=[O:31])[N:14]([C@@H:11]1[CH2:12][CH2:13][N:9]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10]1)[CH3:15])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4250935(Isocyanatomethylene)dibenzeneHCID 70216545(R)-(1-benzoyl-pyrrolidin-3-yl)-methyl-amine

Product 1

HCID 57597560(R)-3-Benzhydryl-1-(1-benzyl-pyrrolidin-3-yl)-1-methyl-ureaYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-(1-benzoyl-pyrrolidin-3-yl)-methyl-amine(0.32 g, 1.68 mmol) in dry CH2Cl2 (5 ml) was added diphenylmethyl isocyanate(0.32 ml, 1.68 mmol) dropwise under nitrogen. The resulting mixture was stirred at room temperature overnight. Removal of solvent under reduced pressure followed by column chromatography using CH2Cl2:CH3OH(15:1) gives 0.65 g of the desired product.

Workup

  1. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-4b9b104873a24f28b297fe2e3acb4c52
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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