Ammonia → (2R)-1-amino-3-(1,2,3,4-tetrahydroisoquinolin-2-yl)propan-2-ol
Reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1.[NH3:15]>CCO>[NH2:15][CH2:3][C@@H:2]([OH:1])[CH2:4][N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of (S)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (2.2 g, 0.012 mol) in EtOH (30 mL), NH3 was bubbled to the solution under −78° C. The reaction mixture was then sealed and heated at 80° C. for 3 h. After LCMS indicated completion of the reaction, the mixture was concentrated and the crude product was used in next step without further purification (2.2 g, Yield 90%). LCMS (m/z): 207.1 (M+1).
Workup
- customThe reaction mixture was then sealed
- customcompletion of the reaction
- concentrationthe mixture was concentrated
- customthe crude product was used in next step without further purification (2.2 g, Yield 90%)
Sources & evidence
- ORD record
- ord-6e17347667724f0b8bd52c81c4a02248
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266836B2
Reaction notes
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