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

HRID 840621노트

반응식

HRID 840621 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6212Chloroform용매HCID 10340Sodium Carbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1722bd91d3bb4acbb573d8ca93e476b8
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369076B1

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