Sodium Hydroxide → (R)-7-azido-1,2,3,4,7,8,9,10-octahydrobenzo[f]isoquinoline

HRID 1444694Notes

Reaction equation

HRID 1444694 reaction equation
[N:1]([C@H:4]1[C:17]2[CH:16]=[CH:15][C:14]3[CH2:13][N:12](C(=O)C(F)(F)F)[CH2:11][CH2:10][C:9]=3[C:8]=2[CH2:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3].[OH-].[Na+]>C1COCC1.CO.O>[N:1]([C@H:4]1[C:17]2[CH:16]=[CH:15][C:14]3[CH2:13][NH:12][CH2:11][CH2:10][C:9]=3[C:8]=2[CH2:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58597280(R)-1-(7-azido-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 58597274(R)-7-azido-1,2,3,4,7,8,9,10-octahydrobenzo[f]isoquinoline

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of (R)-1-(7-azido-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-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 4 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)-7-azido-1,2,3,4,7,8,9,10-octahydrobenzo[f]isoquinoline as a colorless oil.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b3130bf88a8742b08532c1ea92b4ba8a
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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