Methanol → 5-Methoxy-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445365Notes

Reaction equation

HRID 445365 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]=[C:8]2[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1.CO.[BH4-].[Na+]>O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH:8]2[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 59536346HCID 59536346, compound

Product 1

HCID 595362635-Methoxy-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 mL round-bottomed flask was added 5-methoxy-1-(4-(trifluoromethyl)-phenyl)-3,4-dihydroisoquinoline (189 mg, 619 μmol, from step 2), MeOH (3 mL), sodium borohydride (21.8 μL, 619 μmol, Aldrich). The reaction mixture was stirred at RT for 1 h. The reaction mixture was diluted with water (5 mL) and extracted with EtOAc (2×20 mL). The organic extract was washed with saturated NaCl (5 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 80% EtOAc/hexanes to give 5-methoxy-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline. MS (ESI pos. ion) m/z: 308 (M+1).

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. extractionThe organic extract
  3. washwas washed with saturated NaCl (5 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluting with 80% EtOAc/hexanes

Sources & evidence

ORD record
ord-e42ba9c612464a50b4a34383b0162aad
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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