1,8-Diazabicyclo(5.4.0)undec-7-ene → (R/S)-6-(1-azidoethyl)quinoline

HRID 2362609Notes

Reaction equation

HRID 2362609 reaction equation
P([N:17]=[N+:18]=[N-:19])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C1CCN2C(=NCCC2)CC1.[N:31]1[C:40]2[C:35](=[CH:36][C:37]([CH:41](O)[CH3:42])=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1>[N:17]([CH:41]([C:37]1[CH:36]=[C:35]2[C:40](=[CH:39][CH:38]=1)[N:31]=[CH:32][CH:33]=[CH:34]2)[CH3:42])=[N+:18]=[N-:19]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 223480131-(Quinolin-6-yl)ethanol

Product 1

HCID 58270293(R/S)-6-(1-azidoethyl)quinoline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 50 mL round bottom flask under N2 was dissolved diphenyl phosphorazidate (2.44 ml, 11.3 mmol), DBU (1.69 ml, 11.3 mmol) and 1-(quinolin-6-yl)ethanol (1.65 g, 9.53 mmol) (Prepared according to B. P. Lugovkin,/Zhurnal Obshchei Khimii 25 (1955) 392-397) in 20 mL of PhMe stirred at rt for 10 h. The crude mixture was directly purified by MPLC (ISCO) with Hexanes:AcOEt 100:0 to 0:100. MS m/z=199.2 [M+1]+. Calc'd for C11H10N4: 198.1.

Workup

  1. customThe crude mixture was directly purified by MPLC (ISCO) with Hexanes:AcOEt 100:0 to 0:100

Sources & evidence

ORD record
ord-bc1f169e595b4216b100f2f488bd1a12
Source dataset
uspto-grants-2014_04
Patent number
US08691838B2

Reaction notes

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