Sodium borohydride → 5-Amino-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([CH3:13])[CH:7]2[CH3:12].[BH4-].[Na+]>CO>[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:13])[CH:7]2[CH3:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To an ice cold solution of 5-amino-1,2-dihydro-1,2-dimethyl isoquinoline (4 g, 23.2 mmol) in methanol (80 ml) was added sodium borohydride (3.51 g, 92.8 mmol) portionwise. The mixture was allowed to stir at room temperature overnight before concentration in vacuo; the residue was then partitioned between water and dichloromethane. The organic layer was dried over sodium sulfate and concentrated in vacuo to afford a light brown oil (4.023 g).
Workup
- customthe residue was then partitioned between water and dichloromethane
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b4dbccc5d1234b439320822b802a636d
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06277861B1
Reaction notes
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