Water → (1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 445269노트

반응식

HRID 445269 반응식
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[C:21](Cl)(=[O:33])[O:22][C@@H:23]1[CH2:28][C@H:27]([CH3:29])[CH2:26][CH2:25][C@H:24]1[CH:30]([CH3:32])[CH3:31].O>C(Cl)Cl>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]2[C:21]([O:22][C@@H:23]2[CH2:28][C@H:27]([CH3:29])[CH2:26][CH2:25][C@H:24]2[CH:30]([CH3:32])[CH3:31])=[O:33])=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 7014897Carbonochloridic acid, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl esterHCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 59536402(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (100 mg, 0.361 mmol, example 9 (step 3) and (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl carbonochloridate (76.5 μL, 0.361 mmol) in DCM (1 mL) was stirred at RT for 16 h. Then, H2O (2 mL) was added and the mixture was extracted with EtOAc (2×5 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel flash column chromatography (0%-100% EtOAc/hexane) to give the title compound as an off-white oil. MS (ESI, positive ion) m/z: 460 (M+H).

후처리

  1. extractionthe mixture was extracted with EtOAc (2×5 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash column chromatography (0%-100% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-fc9b9113f7674ee3b4d8c025122d7253
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476297B2

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