Acetic Acid → Ethyl (3S, 4aR, 6S, 8aR) 6-(2-cyano-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

HRID 583837노트

반응식

HRID 583837 반응식
O=[C:2]1[CH2:11][CH2:10][CH:9]2[CH:4]([CH2:5][CH:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1.[NH2:21][C:22]1[CH:29]=[CH:28][CH:27]=[C:26](Cl)[C:23]=1[C:24]#[N:25].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClCCCl.[Na].CCCCCC.C(OCC)(=O)C.C(OCC)(=O)C>[C:24]([C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[NH:21][C@H:2]1[CH2:11][CH2:10][C@@H:9]2[C@@H:4]([CH2:5][C@@H:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:7]([C:12]([O:14][CH3:15])=[O:13])[CH2:8]2)[CH2:3]1)#[N:25]

참가 물질

9

반응물 4

HCID 176Acetic AcidHCID 810562-Amino-6-chlorobenzonitrileHCID 516892Sodium BicarbonateHCID 148779783-Ethyl 2-methyl octahydro-6-oxo-2,3(1H)-isoquinolinedicarboxylate

생성물 1

HCID 11485962Ethyl (3S, 4aR, 6S, 8aR) 6-(2-cyano-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate수율 32%

시약·촉매·용매 4

HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매HCID 5360545Sodium용매HCID 21226206Ethyl acetate hexane용매

실험 절차

To a mixture of of ethyl 6-oxo-2-(methoxycarbonyl)-decahydroisoquinoline-3-carboxylate (537 mg, 1.9 mmol), 2-amino-6-chloro-benzonitrile (118 mg, 1.0 mmol), and glacial acetic acid (0.36 mL, 6.0 mmol) in 1,2-dichloroethane (5 mL), sodium triacethoxyborohydride solid (590 mg, 2.8 mmol) was added and the reaction mixture stirred under nitrogen at room temperature for 24 hours. Sodium bicarbonate was added until pH 8, followed by addition of ethyl acetate. The phases were separated and the aqueous phase washed twice with ethyl acetate. The combined organic phases were dried with anhydrous sodium sulfate and concentrated in vacuo. Flash chromatography (silica gel, hexane-ethyl acetate 3:1) afforded 123 mg (32% yield) of the title compound.

후처리

  1. additionwas added
  2. customThe phases were separated
  3. washthe aqueous phase washed twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried with anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-cede956a332046f59582c33f863d02a2
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06924294B2

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