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

HRID 445335Notes

Reaction equation

HRID 445335 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H: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]([C@@H: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 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536297(R)-4-Nitrophenyl 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (1550 mg, 5590 μmol) and diea (1071 μL, 6149 μmol) in DCM (36 mL) at 0° C. was added 4-nitrophenyl chloroformate (1465 mg, 7267 μmol, Aldrich). After addition, the reaction mixture was stirred at RT for overnight. Then, H2O (60 mL) was added and the mixture was stirred at RT for 15 min. The organic layer was collected and the aqueous was extracted with DCM (1×50 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was then mixed with silica gel (4:1, residue: silica gel) and the solid mixture was purified by silica gel flash column chromatography using ISCO instrument (solid loading, 0%-100% EtOAc/hexane) to give the compound as an off-white solid. MS (ESI, positive ion) m/z: 443 (M+H).

Workup

  1. additionAfter addition
  2. stirringthe mixture was stirred at RT for 15 min
  3. customThe organic layer was collected
  4. extractionthe aqueous was extracted with DCM (1×50 mL)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated
  7. additionThe residue was then mixed with silica gel (4:1, residue: silica gel)
  8. customthe solid mixture was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-25e9e608ec5d4a598b46cd40fe29f696
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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