Sodium Hydroxide → (R)-6-azido-1,2,3,4,6,7,8,9-octahydrobenzo[g]isoquinoline

HRID 1444700Notes

Reaction equation

HRID 1444700 reaction equation
[N:1]([C@H:4]1[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][C:8]=2[CH2:7][CH2:6][CH2:5]1)[CH2:15][N:14](C(=O)C(F)(F)F)[CH2:13][CH2:12]3)=[N+:2]=[N-:3].[OH-].[Na+]>C1COCC1.CO.O>[N:1]([C@H:4]1[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][C:8]=2[CH2:7][CH2:6][CH2:5]1)[CH2:15][NH:14][CH2:13][CH2:12]3)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58597252(R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 58597282(R)-6-azido-1,2,3,4,6,7,8,9-octahydrobenzo[g]isoquinoline

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of (R)-1-(6-azido-3,4,6,7,8,9-hexahydrobenzo[g]-isoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone (972 mg, 3.0 mmol) and NaOH (240 mg, 6 mmol) in 21 mL of THF/MeOH/H2O (10/10/1) was stirred at RT for 5 h. The solvent was evaporated and the residue was submitted to flash chomatograph (SiO2, EtOAc/MeOH=100:10 to 100:20 to 100:30) to give (R)-6-azido-1,2,3,4,6,7,8,9-octahydrobenzo[g]isoquinoline as a colorless oil.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0830e3388d494b508d26f930f056b8a9
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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