Allyl Alcohol → HCID 58431049, compound

HRID 1672035Notes

Reaction equation

HRID 1672035 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].C([O:37][CH2:38]C)(=O)C>C1(C)C=CC=CC=1.O>[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1([NH:27][C:38](=[O:37])[O:33][CH2:30][CH:31]=[CH2:32])[CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 7858Allyl AlcoholHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 584310521-(Pyrazin-2-yl)cyclopropane-1-carboxylic acid

Product 1

HCID 58431049HCID 58431049, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-(pyrazin-2-yl)cyclopropanecarboxylic acid (0.18 g, 1.09 mmol, 1 eq) in dry toluene (5 ml) was added TEA (0.18 ml, 1.3 mmol, 1.2 eq) followed by diphenylphosphoryl azide (0.25 ml, 1.18 mmol, 1.08 eq). The reaction was stirred for 1 h at r.t. Allyl alcohol (0.36 ml, 5.30 mmol, 4.9 eq) was added via syringe and the reaction was heated to 90° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with water (10 ml) and ethyl acetate (10 ml). The layers were separated and the water layer was extracted with ethyl acetate (2×10 ml). The combined organic layers were dried over Na2SO4 and concentrated to give a black residue that was purified by silica column chromatography using 20-30% ethyl acetate in hexane. Yield: 0.12 g (50%). 1H NMR (400 MHz, CD3OD): δ 1.31-1.38 (m, 2H), 1.60-1.63 (m, 2H), 4.60-4.61 (d, J=5.2 Hz, 2H), 5.23-5.26 (d, J=10.4 Hz, 1H), 5.35-5.39 (d, J=17.2 Hz, 1H,), 5.96-6.03 (m, 1H), 8.36-8.36 (d, J=2.4 Hz, 1H), 8.49-8.508 (q, 1H), 8.63 (s, 1H). LCMS: (ES+) m/z=220.2 (M+H)+

Workup

  1. temperaturethe reaction was heated to 90° C. for 3 h
  2. temperatureAfter cooling to room temperature
  3. customThe layers were separated
  4. extractionthe water layer was extracted with ethyl acetate (2×10 ml)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customto give a black residue that
  8. customwas purified by silica column chromatography

Sources & evidence

ORD record
ord-121106e228e340daa65c88deb8641219
Source dataset
uspto-grants-2011_08
Patent number
US07994171B2

Reaction notes

Loading…