Allyl Alcohol → HCID 58431049, compound
Reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1(C(O)=O)[CH2:9][CH2:8]1.C1(P([N:27]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:30]([OH:33])[CH:31]=[CH2:32].CCO[C:37](C)=[O:38]>C1(C)C=CC=CC=1.O>[CH2:30]([O:33][C:37](=[O:38])[NH:27][C:7]1([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[CH2:8][CH2:9]1)[CH:31]=[CH2:32]Participants
Procedure
To a solution of 1-Pyrazin-2-yl-cyclopropanecarboxylic acid (111 mg, 0.676 mmol) in dry toluene (1.5 mL) was added TEA (0.11 mL, 0.81 mmol) followed by diphenylphosphoryl azide (DPPA, 0.16 mL, 0.74 mmol). The reaction was stirred for 1 h at rt. Allyl alcohol (0.2 mL) was added via syringe and the reaction was heated to 90° C. for 3 h. After cooling to room temperature, the reaction was diluted with water (6 mL) and EtOAc (4 mL). The layers were separated and the water layer was extracted with EtOAc (3×4 mL). The combined organic layers were dried over Na2SO4 and concentrated to give a black residue that was purified by flash chromatography (silica, 40→50% EtOAc/hexanes) to give 67 mg of the title compound as a light orange oil, m/z 220.52 [M+1]+.
Workup
- temperaturethe reaction was heated to 90° C. for 3 h
- temperatureAfter cooling to room temperature
- customThe layers were separated
- extractionthe water layer was extracted with EtOAc (3×4 mL)
- dry with materialThe combined organic layers were dried over Na2SO4
- concentrationconcentrated
- customto give a black residue that
- customwas purified by flash chromatography (silica, 40→50% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-b3292982ab6441609b16d74697bd8cd4
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552205B2
Reaction notes
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