2-(1,2,3,4-Tetrahydroisoquinolin-2-yl)ethan-1-amine → 2-[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-4-nitro-2,3-dihydroisoindol-1-one

HRID 914973

反応式

HRID 914973 の反応式
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][NH2:13].Br[CH2:15][C:16]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][C:17]=1[C:18](OCC)=[O:19].C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]1[CH2:11][CH2:12][N:13]1[CH2:15][C:16]2[C:17](=[CH:23][CH:24]=[CH:25][C:26]=2[N+:27]([O-:29])=[O:28])[C:18]1=[O:19]

参加物

5

反応物 3

HCID 407422-(1,2,3,4-Tetrahydroisoquinolin-2-yl)ethan-1-amineHCID 516892Sodium BicarbonateHCID 19788106Ethyl 2-(bromomethyl)-3-nitrobenzoate

生成物 1

HCID 589581672-[2-(3,4-Dihydro-1H-isoquinolin-2-yl)ethyl]-4-nitro-2,3-dihydroisoindol-1-one収率 57.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(3,4-dihydro-1H-isoquinolin-2-yl)ethylamine (36) (0.36 g, 2.0 mmol) in dichloromethane (4 mL) was added the bromide 35 (0.75 g, 2.6 mmol) in dichloromethane (5 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 16 hours before it was poured into saturated NaHCO3 (aq. 50 mL) and extracted with dichloromethane (2×50 mL). The combined organic layers were washed with water (70 mL), brine (70 mL), dried over MgSO4, and concentrated on a rotavap. The residue was chromatographed on silica gel eluting with 3:1 to 1:1 hexanes/EtOAc to give 37 (0.39 g, 57%).

後処理

  1. extractionextracted with dichloromethane (2×50 mL)
  2. washThe combined organic layers were washed with water (70 mL), brine (70 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated on a rotavap
  5. customThe residue was chromatographed on silica gel eluting with 3:1 to 1:1 hexanes/EtOAc

出典と根拠

ORDレコード
ord-816dd867aafd4d0cb2776ca8a6302be5
出典データセット
uspto-grants-2007_09
特許番号
US07265122B2

関連ノート

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