Sodium borohydride → 4,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445285Notes

Reaction equation

HRID 445285 reaction equation
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:4][CH2:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=2)[NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 595364234,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

Product 1

HCID 595363404,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 50-mL round-bottomed flask was charged with 4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (2.52 g, 8.3 mmol) and dry MeOH (10 mL). After cooling down to 0° C. sodium borohydride (943 mg, 24.9 mmol) was added and the mixture was stirred at RT for 45 min. Then, the solvent was removed and the residue redissolved in EtOAc, washed with sat NaHCO3, water and dried over Na2SO4. The residue was purified by silica gel chromatography (25-35% EtOAc in hexanes) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 306 (M+H).

Workup

  1. additionwas added
  2. customThen, the solvent was removed
  3. dissolutionthe residue redissolved in EtOAc
  4. washwashed
  5. dry with materialdried over Na2SO4
  6. customThe residue was purified by silica gel chromatography (25-35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-f2c24425ee0f4b778565f1a525ae121d
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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