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

HRID 1640724ノート

反応式

HRID 1640724 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9581f43c9722405aaf02ed7f6f8f4ef0
出典データセット
uspto-grants-2012_02
特許番号
US08114868B2

反応ノート

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