1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86612599, compound

HRID 1784923Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH2:15]O)[CH:12]=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P([N:31]=[N+:32]=[N-:33])(C2C=CC=CC=2)=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:31]([CH2:15][C:11]1[CH:12]=[N:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)=[N+:32]=[N-:33]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 250 mg (1.17 mmol) of (5-(benzyloxy)pyridin-3-yl)methanol in 8 mL of toluene was added 310 μL (1.44 mmol) of DPPA. The mixture was cooled to 0° C. and 210 μL (1.44 mmol) of 1,8-diazabicyclo[5.4.0]-undec-7-ene] (DBU) was added. The ice bath was removed, and stirring was continued with wanning to room temperature. After about 20 h, the solution was diluted with EtOAc, and 1N HCl was added to a pH between 7 and 8. The organic layer was washed with water (2×15 mL) and brine (15 mL) and dried over Na2SO4. After filtration and concentration, the crude product was purified by flash silica gel chromatography (56-60% EtOAc/hexanes) to give 181 mg (65% yield) of the azide as a colorless oil.

Workup

customThe ice bath was removed
customwith wanning to room temperature
additionthe solution was diluted with EtOAc, and 1N HCl
additionwas added to a pH between 7 and 8
washThe organic layer was washed with water (2×15 mL) and brine (15 mL)
dry with materialdried over Na2SO4
filtrationAfter filtration and concentration
customthe crude product was purified by flash silica gel chromatography (56-60% EtOAc/hexanes)

Sources & evidence

ORD record: ord-0b698925d96c4693929fae997b8485d2
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504420B2

Reaction notes

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