Ammonia → (S)-1-Amino-3-(3,4-dihydroisoquinolin-2(1H)-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]1

Participants

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

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

Sources & evidence

ORD record: ord-83420e05e74647a89f40873bffc30c6b
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940726B2

Reaction notes

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Participants

Reactant 2

HCID 222Ammonia

HCID 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