1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-Allyl-6-phenyl-3-(2-phenylcyclopropyl)-1,3-oxazinan-2-one

HRID 450967Notes

Reaction equation

HRID 450967 reaction equation
[N:1]([CH:4]1[CH2:6][CH:5]1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[C:2]=[O:3].C1CCN2C(=NCCC2)CC1.Cl[CH2:25][CH2:26][C:27]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([OH:31])[CH2:28][CH:29]=[CH2:30]>C1COCC1.CCOC(C)=O>[CH2:28]([C:27]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:31][C:2](=[O:3])[N:1]([CH:4]2[CH2:6][CH:5]2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:25][CH2:26]1)[CH:29]=[CH2:30]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 582709(2-Isocyanatocyclopropyl)benzeneHCID 159334751-Chloro-3-phenylhex-5-en-3-ol

Product 1

HCID 595323586-Allyl-6-phenyl-3-(2-phenylcyclopropyl)-1,3-oxazinan-2-oneYield 7.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2-isocyanatocyclopropyl)benzene (800 mg, 5.03 mmol) in THF (15 mL) was added DBU (1.61 g, 10.48 mmol) and 1-chloro-3-phenylhex-5-en-3-ol (880 mg, 4.19 mmol), and the mixture was refluxed overnight. The solution was diluted with EtOAc, and washed with 1 N HCl (2×15 mL). The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give crude product, which was purified by preparative TLC to afford 6-allyl-6-phenyl-3-(2-phenylcyclopropyl)-1,3-oxazinan-2-one (100 mg, 6%). 1H NMR (CDCl3): 1.05-1.21 (m, 3H), 1.36-1.42 (m, 1H), 2.13-2.34 (m, 1H), 2.39-2.61 (m, 2H), 2.92-3.15 (m, 1H), 3.76-4.01 (m, 1H), 4.95-5.10 (m, 2H), 5.42-5.73 (m, 1H), 6.95-6.99 (m, 1H), 7.10-7.24 (m, 10H).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. washwashed with 1 N HCl (2×15 mL)
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-c4483ef8bc41484aa61e4c08c0aa43c2
Source dataset
uspto-grants-2013_07
Patent number
US08487094B2

Reaction notes

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