Sodium Acetate → 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one

HRID 840621ノート

反応式

HRID 840621 の反応式
C(O[C:4](=[O:21])[CH2:5][CH2:6][CH:7]1[CH2:12][CH:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][C:8]1=O)C.Cl.Cl.[NH2:24][CH2:25][C:26]1[NH:27][C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=1.C([O-])(=O)C.[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].ClCCCl>[NH:27]1[C:28]2[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=2[N:30]=[C:26]1[CH2:25][N:24]1[CH:8]2[CH:7]([CH2:12][CH:11]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:5][C:4]1=[O:21]

参加物

8

反応物 4

HCID 517045Sodium AcetateHCID 2723957(1H-benzo[d]imidazol-2-yl)methanamine dihydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 699404643-(5-Benzyl-2-oxo-cyclohexyl)-propionic acid ethyl ester

生成物 1

HCID 99075681-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one収率 15.7%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 6212Chloroform溶媒HCID 10340Sodium Carbonate溶媒

実験手順

A mixture of 0.74 g of 3-(5-benzyl-2-oxo-cyclohexyl)-propionic acid ethyl ester, 0.572 g of 2-aminomethylbenzimidazole dihydrochloride, 10 mL of 1,2-dichloroethane, 0.40 g of sodium acetate and 0.74 g of sodium triacetoxyborohydride was stirred at room temperature for 48 h. The reaction mixture was diluted with 100 mL chloroform and 40 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 2×25 mL of chloroform and the combined organic layers dried over magnesium sulfate and concentrated under reduced pressure. Purification by chromatography eluting with a gradient of ethyl acetate to 10% methanol in ethyl acetate gave 0.15 g of 1-(1H-benzimidazol-2-ylmethyl)-6-benzyl-octahydro-quinolin-2-one.

後処理

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×25 mL of chloroform
  3. dry with materialthe combined organic layers dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography
  6. washeluting with a gradient of ethyl acetate to 10% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-1722bd91d3bb4acbb573d8ca93e476b8
出典データセット
uspto-grants-2002_04
特許番号
US06369076B1

反応ノート

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