Ammonia → (S)-1-Amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol

HRID 880299Notes

Reaction equation

HRID 880299 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]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 30076569(R)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 25312355(S)-1-Amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-olYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (15 g, 0.08 mol) in EtOH (100 mL) at −78° C. was slowly bubbled NH3 (g). The reaction mixture was then sealed and heated at 80° C. for 3 h. The reaction mixture was concentrated and the crude product was used in next step without further purification (15 g, Yield 92%). LCMS (m/z): 207.1 (M+1).

Workup

  1. customat −78° C.
  2. customThe reaction mixture was then sealed
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude product was used in next step without further purification (15 g, Yield 92%)

Sources & evidence

ORD record
ord-2183d4af4c4a46eca118f30d81e61287
Source dataset
uspto-grants-2015_03
Patent number
US08993555B2

Reaction notes

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