1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(1-Azido-2-(1,3-dioxolan-2-yl)ethyl)-2-(trifluoromethyl)pyridine

HRID 657741Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH:7]([C:9]1[CH:10]=[N:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1)O.C1C=CC(OP(OC2C=CC=CC=2)([N:28]=[N+:29]=[N-:30])=O)=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:28]([CH:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[N:11][CH:10]=1)[CH2:6][CH:2]1[O:3][CH2:4][CH2:5][O:1]1)=[N+:29]=[N-:30]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-(1,3-dioxolan-2-yl)-1-(6-(trifluoromethyl)pyridin-3-yl)ethanol (18.54 g, 0.070 mol) and diphenylphosphonic azide (36 mL, 0.17 mol) in toluene (40 mL) was cooled to 0° C. and neat 1,8-diazabicyclo[5.4.0]undec-7-ene (25 mL, 0.17 mol) was added. The reaction mixture was stirred at 0° C. for 2 hr and then at 20° C. overnight. The mixture was washed with water and 5% HCl. The aqueous phase was extracted with CH2Cl2. The combined orangic layers were concentrated in vacuo and the residue was purified by silica gel column (0-100% EtOAc/hexane) to afford a colorless oil.

Workup

customat 20° C.
customovernight
washThe mixture was washed with water and 5% HCl
extractionThe aqueous phase was extracted with CH2Cl2
concentrationThe combined orangic layers were concentrated in vacuo
customthe residue was purified by silica gel column (0-100% EtOAc/hexane)
customto afford a colorless oil

Sources & evidence

ORD record: ord-bf508e8931b1442ba6a01616a9add46d
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076345B2

Reaction notes

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