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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
ノート
印刷プレビュー

反応式

HRID 1181588 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-05c148326ee949cd9807edd75191c042
出典データセット
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07285572B2

反応ノート

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