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

HRID 445290Notes

Reaction equation

HRID 445290 reaction equation
[CH3:1][CH:2]1[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][CH:2]1[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 595364124-Methyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

Product 1

HCID 595362814-Methyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A 100-mL round-bottomed flask was charged with 4-methyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (4.89 g, 16.9 mmol) and MeOH (30 mL). After cooling down to 0° C., sodium borohydride (1.93 g, 50.7 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 mixture was used crude in the next step.

Workup

  1. customThen, the solvent was removed
  2. dissolutionthe residue redissolved in EtOAc
  3. washwashed
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-4fd6007c20b24da0a105220a2c944376
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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