1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-(4-Fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-one

HRID 1640724노트

반응식

HRID 1640724 반응식
Cl[CH2:2][CH2:3][C:4]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)([OH:9])[CH2:5][C:6]([CH3:8])=[CH2:7].BrC1C=CC=CC=1[C@@H]([N:26]=[C:27]=[O:28])C.C1CCN2C(=NCCC2)CC1>C1COCC1.CCOC(C)=O>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:4]2([CH2:5][C:6]([CH3:8])=[CH2:7])[O:9][C:27](=[O:28])[NH:26][CH2:2][CH2:3]2)=[CH:11][CH:12]=1

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 596356741-Chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-olHCID 86649409(S)-(-)-1-(-bromophenyl)ethyl isocyanate

생성물 1

HCID 866494086-(4-Fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-one수율 65.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1-chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-ol (3.15 g, 13 mmol), (S)-(−)-1-(-bromophenyl)ethyl isocyanate (3.5 g, 16 mmol), and DBU (8 g, 33 mmol) in THF (80 mL) was heated to reflux for 25 h. The mixture was diluted with EtOAc and washed with 1 N aq HCl. The aqueous phase was extracted with EtOAc (3 x). The combined organic phase was dried over Na2SO4. After the solvents were evaporated, the crude product was purified by column to give (R)-3-(S)-1-(4-bromophenyl)-ethyl)-6-(4-fluorophenyl)-6-(2-methylallyl)-1,3-oxazinan-2-one (2.13 g, yield: 38%).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 25 h
  3. washwashed with 1 N aq HCl
  4. extractionThe aqueous phase was extracted with EtOAc (3 x)
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. customAfter the solvents were evaporated
  7. customthe crude product was purified by column

출처 및 근거

ORD 기록
ord-9581f43c9722405aaf02ed7f6f8f4ef0
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114868B2

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