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

HRID 2201994Notes

Reaction equation

HRID 2201994 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.[NH4+:15].[OH-]>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 14923Ammonium HydroxideHCID 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-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (R)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (200 mg, 5.2 mmol) in EtOH (20 mL) was added NH4OH (600 mg, 35.2 mmol) at −78° C. The reaction mixture was then warmed and heated at 100° C. for 3 h in a seal tube. The reaction mixture was concentrated and the crude product was used in next step without further purification. LCMS (m/z): 207.1 (M+1).

Workup

  1. temperatureThe reaction mixture was then warmed
  2. concentrationThe reaction mixture was concentrated
  3. customthe crude product was used in next step without further purification

Sources & evidence

ORD record
ord-e59f085548d347d1919057f5d728d73b
Source dataset
uspto-grants-2016_06
Patent number
US09365519B2

Reaction notes

Loading…