Dichloromethane → HCID 86628565, compound

HRID 732722Notes

Reaction equation

HRID 732722 reaction equation
[C:1]1([C@H:11]([N:13]([CH2:21][CH:22]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][NH:24][CH2:23]2)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClCCl.[C:36]1([N:42]=[C:43]=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(OCC)(=O)C>[NH:42]([C:43]([N:24]1[CH2:25][CH:26]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:22]([CH2:21][N:13]([C@@H:11]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[CH3:12])[C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17])[CH2:23]1)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7672Phenyl isocyanateHCID 86628564HCID 86628564, compound

Product 1

HCID 86628565HCID 86628565, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 215 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl][(4-phenylpyrrolidin-3-yl)methyl]carbamate and 5 ml of dichloromethane was mixed with 119 mg of phenyl isocyanate and stirred at room temperature for 4 hours. The reaction solution was diluted with ethyl acetate and washed with water and 1 M hydrochloric acid. The organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)to obtain 270 mg of crude tert-butyl {[1-(anilinocarbonyl)-4-phenylpyrrolidin-3-yl]methyl}[(1R)-1-(1-naphthyl)ethyl]carbamate as a colorless solid. The thus obtained compound was dissolved in 5 ml of ethyl acetate, mixed with 1 ml of 4 M hydrogen chloride/ethyl acetate and stirred overnight at room temperature. The resulting precipitate was collected by filtration to obtain 56 mg of 3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-N,4-diphenylpyrrolidine-1-carboxamide hydrochloride as a white solid.

Workup

  1. washwashed with water and 1 M hydrochloric acid
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated under a reduced pressure
  4. customThe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-806ef3e943ec452681a1bdd935d803b9
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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