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

HRID 2070980Notes

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 warming 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 3-(azidomethyl)-5-(benzyloxy)pyridine as a colorless oil.

Workup

customThe ice bath was removed
temperaturewith warming 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-0af6e61f1fa9431faeb2d966a2fdee6a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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