1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57885538, compound

HRID 1819451Notes

Reaction equation

HRID 1819451 reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([CH2:11]O)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1C=CC(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.Cl.C(OCC)(=O)C>[N:27]([CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2)=[N+:28]=[N-:29]

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 823080(Quinolin-5-yl)methanol

Product 1

HCID 57885538HCID 57885538, compoundYield 44.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of quinolin-5-yl-methanol (96 mg, 0.60 mmol) and DPPA (202 μL, 0.91 mmol) in toluene (2 mL) was added DBU (166 μL, 1.09 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with 3M HCl (1.7 mL) and ethyl acetate (5 mL). The organic phase was separated and the aqueous phase was re-extracted with ethyl acetate (×2). The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 49 mg of 5-azidomethyl-quinoline as light brown oil (44%).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was re-extracted with ethyl acetate (×2)
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-4cfb284856e1495aba866dc386d6f8b5
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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