Water → 4-Nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 445263

Reaction equation

HRID 445263 reaction equation
[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.CCN(C(C)C)C(C)C.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=1)=[O:32].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:31]([O:33][C:34]2[CH:35]=[CH:36][C:37]([N+:40]([O-:42])=[O:41])=[CH:38][CH:39]=2)=[O:32])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 166406961-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 426351024-Nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (200 mg, 0.721 mmol, example 9 (step 3) and DIEA (126 μL, 0.721 mmol) in DCM (4 mL) was added 4-nitrophenyl chloroformate (145 mg, 0.721 mmol). The resulting mixture was stirred at RT for 16 h. Then, H2O (10 mL) was added and the mixture was extracted with DCM (2×5 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel flash column chromatography (0%-50% EtOAc/hexane) to give the title compound as a white oil. MS (ESI, positive ion) m/z: 443 (M+H).

Workup

  1. extractionthe mixture was extracted with DCM (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%-50% EtOAc/hexane)

Sources & evidence

ORD record
ord-af957338c2bb4a96a53b585316e744ee
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Linked notes

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