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Pyridine → (1S,6R,9aR)-6-(3,4-difluorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

HRID 16387
ノート
印刷プレビュー

反応式

HRID 16387 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[NH:14][C@@H:13]([CH:15]([OH:17])[CH3:16])[CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].N1C=CC=CC=1.[C:24](Cl)(=[O:28])[C:25](Cl)=[O:26]>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[CH2:10][O:11][CH2:12][C@@H:13]3[C@H:15]([CH3:16])[O:17][C:24](=[O:28])[C:25](=[O:26])[N:14]23)[CH:5]=[CH:6][C:7]=1[F:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 673752911-[(3R,5R)-5-(3,4-difluorophenyl)morpholin-3-yl]ethanol

生成物 1

HCID 67372582(1S,6R,9aR)-6-(3,4-difluorophenyl)-1-methyltetrahydro-[1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344
Dichloromethane
溶媒

実験手順

To a solution consisting of 1-[(3R,5R)-5-(3,4-difluorophenyl)morpholine-3-yl]ethanol (424 mg) and pyridine (2 mL) in dichloromethane (8 mL) was dropwise added oxalyl chloride (417 μL) while cooling with ice. The resultant solution was stirred at the same temperature for 30 minutes. The reaction solution was diluted with water, and the organic layer was partitioned. The organic layer was then dried over magnesium sulfate. Solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/4), to thereby obtain the titled compound (353 mg). The physical properties of the compound were as follows.

後処理

  1. temperaturewhile cooling with ice
  2. customthe organic layer was partitioned
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. customSolvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/4)

出典と根拠

ORDレコード
ord-257e7e727ab7428bbfc3c4d84c9c9624
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737141B2

反応ノート

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