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alpha,alpha-Dimethyl-2-naphthaleneethanamine → Methyl 3-[2-[(1R)-1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]phenyl]propionate

HRID 1181588
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HRID 1181588 반응식
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH3:7].[CH3:20][C:21]([NH2:34])([CH3:33])[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[OH:1][C@H:2]([CH2:3][NH:34][C:21]([CH3:33])([CH3:20])[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[CH2:4][O:5][C@@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH3:7]
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참가 물질

5

반응물 3

HCID 15369616alpha,alpha-Dimethyl-2-naphthaleneethanamineHCID 23665649Lithium perchlorateHCID 58662605methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propionate

생성물 1

HCID 58662623Methyl 3-[2-[(1R)-1-[(2R)-2-hydroxy-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propoxy]ethyl]phenyl]propionate수율 107.4%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

Methyl 3-[2-[(1R)-1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propionate (286 mg) obtained in Step 3 was dissolved in acetonitrile (10 ml), [2-methyl-1-(naphthalen-2-yl)propan-2-yl]amine (218 mg) and lithium perchlorate (157 mg) were successively added, and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (539 mg).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

출처 및 근거

ORD 기록
ord-05c148326ee949cd9807edd75191c042
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07285572B2

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