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

HRID 732729노트

반응식

HRID 732729 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-41da784be8ca4e3f8064cc66b741faee
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585886B2

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