1,1-Dichloroethane → 4-({[(1R)-1-(3-methoxyphenyl)ethyl]amino}methyl)-1-phenylpyrrolidin-2-one hydrochloride

HRID 732729Notes

Reaction equation

HRID 732729 reaction equation
[Cl:1]C(Cl)C.[O:5]=[C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9][CH:8]([CH:17]=O)[CH2:7]1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C@H:27]([NH2:29])[CH3:28])[CH:24]=[CH:25][CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O.C(O)(=O)C>[ClH:1].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C@H:27]([NH:29][CH2:17][CH:8]2[CH2:9][N:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:6](=[O:5])[CH2:7]2)[CH3:28])[CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamineHCID 866285405-Oxo-1-phenylpyrrolidine-3-carboaldehyde

Product 1

HCID 689124624-({[(1R)-1-(3-methoxyphenyl)ethyl]amino}methyl)-1-phenylpyrrolidin-2-one hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A 10 ml dichloroethane solution of 0.53 g of 5-oxo-1-phenylpyrrolidine-3-carboaldehyde was mixed with 508 mg of (1R)-1-(3-methoxyphenyl)ethanamine and 0.1 ml of acetic acid and stirred at room temperature for 1 hour. Successively this was mixed with 1.8 g of sodium triacetoxyborohydride and stirred overnight at room temperature. This was mixed with 40 ml of water and extracted with chloroform. The organic layer was concentrated, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol), treated with 4 M hydrogen chloride/ethyl acetate and concentrated to dryness to obtain 161 mg of 4-({[(1R)-1-(3-methoxyphenyl)ethyl]amino}methyl)-1-phenylpyrrolidin-2-one hydrochloride as a colorless solid.

Workup

  1. stirringstirred overnight at room temperature
  2. extractionextracted with chloroform
  3. concentrationThe organic layer was concentrated
  4. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)
  5. additiontreated with 4 M hydrogen chloride/ethyl acetate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-41da784be8ca4e3f8064cc66b741faee
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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