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

HRID 450967ノート

反応式

HRID 450967 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c4483ef8bc41484aa61e4c08c0aa43c2
出典データセット
uspto-grants-2013_07
特許番号
US08487094B2

反応ノート

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