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

HRID 445369Notes

Reaction equation

HRID 445369 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]=[C:7]2[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1.CO.[BH4-].[Na+]>O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH:7]2[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 595362925-Bromo-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

Product 1

HCID 595362725-Bromo-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round-bottomed flask was added 5-bromo-1-(4-(trifluoromethyl)-phenyl)-3,4-dihydroisoquinoline (1.18 g, 3332 μmol, from step 2), MeOH (5 mL), sodium borohydride (117 μL, 3332 μmol, Aldrich). The reaction mixture was stirred at RT for 1 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with water (20 mL), saturated NaCl (20 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 40% EtOAc/hexanes to give 5-bromo-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline. MS (ESI pos. ion) m/z: 356 (M+1).

Workup

  1. extractionextracted with EtOAc (2×40 mL)
  2. extractionThe organic extract
  3. washwas washed with water (20 mL), saturated NaCl (20 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 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-c0e6b8f43f1b43408cd0cd31c308f932
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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