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

HRID 445269Notes

Reaction equation

HRID 445269 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.[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-fc9b9113f7674ee3b4d8c025122d7253
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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