Methanol → (2-(2,2,2-Trifluoroethyl)-1,2,3,4-tetrahydroisoquinolin-8-yl)methanol

HRID 920222Notes

Reaction equation

HRID 920222 reaction equation
C([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH2:14][N:13]([CH2:16][C:17]([F:20])([F:19])[F:18])[CH2:12][CH2:11]2)(=O)C.CO.C([O-])([O-])=O.[K+].[K+]>O>[F:20][C:17]([F:18])([F:19])[CH2:16][N:13]1[CH2:12][CH2:11][C:10]2[C:15](=[C:6]([CH2:5][OH:4])[CH:7]=[CH:8][CH:9]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 89526139(2-(2,2,2-Trifluoroethyl)-1,2,3,4-tetrahydroisoquinolin-8-yl)methyl acetate

Product 1

HCID 89526014(2-(2,2,2-Trifluoroethyl)-1,2,3,4-tetrahydroisoquinolin-8-yl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 5 dram vial, added 7-4 (21.7 mg, 0.076 mmol) to methanol (504 μl) and water (252 μl). Added K2CO3 (52.2 mg, 0.378 mmol) and allowed to stir at RT. After 1 h at RT, LCMS showed complete consumption of SM to desired product. Partitioned reaction contents into 10 mL EtOAc+5 mL H2O. Separated layers, back-extracted aqueous with 3×5 mL EtOAc. Dried combined organics over Na2SO4, filtered, concentrated to give 7-5 as a pale yellow oil. Carried crude material forward to subsequent step.

Workup

  1. customconsumption of SM to desired product
  2. customPartitioned
  3. customreaction contents into 10 mL EtOAc+5 mL H2O
  4. extractionSeparated layers, back-extracted aqueous with 3×5 mL EtOAc
  5. customDried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d229938c1fdd4f63ad900959fdaca016
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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