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

HRID 450967

반응식

HRID 450967 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c4483ef8bc41484aa61e4c08c0aa43c2
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487094B2

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