1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal → 2-{4-[[1-(3-Methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

HRID 251205

反応式

HRID 251205 の反応式
[CH3:1][C:2]1[C:3]([CH:8]([NH2:10])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[O:11]=[C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[N:13]1[CH2:22][CH2:23][CH2:24][CH:25]=O.[BH-](O[C:37]([CH3:39])=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][C:2]1[C:3]([CH:8]([N:10]([CH:39]2[C:37]3[N:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH2:3][CH2:8][CH2:9]2)[CH2:25][CH2:24][CH2:23][CH2:22][N:13]2[C:14](=[O:21])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:12]2=[O:11])[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanalHCID 5049666Sodium triacetoxyborohydrideHCID 457911661-(3-Methylpyridin-2-yl)ethan-1-amine

生成物 1

HCID 672725222-{4-[[1-(3-Methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of the above amine and 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyraldehyde (127 mg, 0.58 mmol) in CH2Cl2 (2.5 mL) was added NaBH(OAc)3 (117 mg, 0.55 mmol) and the reaction was stirred at room temperature under N2 for 16 hours. The mixture was diluted with saturated aqueous NaHCO3 (10 mL) and was extracted with CH2Cl2 (10 mL×3). The combined organic solution was dried (MgSO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH, 9:1) gave 2-{4-[[1-(3-methyl-pyridin-2-yl)-ethyl]-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione as a 1:1 mixture of two diastereomers (72 mg, 0.15 mmol, 43%) along with some single diastereomer (33 mg, 0.07 mmol, 20%).

後処理

  1. extractionwas extracted with CH2Cl2 (10 mL×3)
  2. dry with materialThe combined organic solution was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography on silica (CH2Cl2/MeOH, 9:1)

出典と根拠

ORDレコード
ord-f0f15f6ef15d4b0cb2055b86bf23ad42
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

関連ノート

読み込み中…