Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate → Benzyl-4-(3-hydroxy-6-methoxy-2-methyl-1-oxo-4-phenyl-1,2,3,4-tetra-hydroisoquinolin-3-yl)piperidine-1-carboxylate

HRID 17871

반응식

HRID 17871 반응식
C(O)(C)C.C(=O)=O.[CH3:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][CH3:17])=[O:15])=[C:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:11]=1.C([Li])(CC)C.[CH2:32]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([C:48](Cl)=[O:49])[CH2:44][CH2:43]1)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH2:32]([O:39][C:40]([N:42]1[CH2:47][CH2:46][CH:45]([C:48]2([OH:49])[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]3[C:13](=[CH:18][CH:19]=[C:10]([O:9][CH3:8])[CH:11]=3)[C:14](=[O:15])[N:16]2[CH3:17])[CH2:44][CH2:43]1)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

7

반응물 4

HCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateHCID 225559272-Benzyl-4-methoxy-N-methylbenzamideHCID 86586944Isopropanol carbon dioxideHCID 178418400CID 53628100

생성물 1

HCID 68433490Benzyl-4-(3-hydroxy-6-methoxy-2-methyl-1-oxo-4-phenyl-1,2,3,4-tetra-hydroisoquinolin-3-yl)piperidine-1-carboxylate수율 49.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 21226206Ethyl acetate hexane용매

실험 절차

To an isopropanol/dry ice cooled solution of 4-Methoxy-N-methyl-2-(phenylmethyl)benzamide (250 mg, 0.980 mmol) in THF (50 mL) under argon was added sec-butyllithium solution (1.3M, 1.55 mL, 2.00 mmol) dropwise. After 10 min. a THF (10 mL) solution of benzyl-4-(chlorocarbonyl)piperidine-1-carboxylate (275 mg, 980 mmol) was quickly added to the reaction solution. After 10 min. the reaction was quenched with water then warmed to room temperature. Saturated sodium bicarbonate was added and the resulting mixture extracted with ethyl acetate (3×) and dried with anhydrous magnesium sulfate. Filtration followed by evaporation of solvent in vacuo gave the crude product which was subjected to flash column chromatography (hexane:ethyl acetate 50:50) to afford benzyl-4-(3-hydroxy-6-methoxy-2-methyl-1-oxo-4-phenyl-1,2,3,4-tetra-hydroisoquinolin-3-yl)piperidine-1-carboxylate as a white foam (242 mg, 0.484 mmol, 49%). MS [M+H]+ 501.2

후처리

  1. customAfter 10 min. the reaction was quenched with water
  2. additionSaturated sodium bicarbonate was added
  3. extractionthe resulting mixture extracted with ethyl acetate (3×)
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation of solvent in vacuo
  7. customgave the crude product which

출처 및 근거

ORD 기록
ord-cdf90ed4d8804be8853d1f11965f5421
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741322B2

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