Pyridine → (6R,9aR)-1,1-dimethyl-6-(3,4,5-trifluorophenyl)tetrahydro [1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

HRID 16392ノート

反応式

HRID 16392 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[NH:15][C@@H:14]([C:16]([OH:19])([CH3:18])[CH3:17])[CH2:13][O:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].N1C=CC=CC=1.[C:26](Cl)(=[O:30])[C:27](Cl)=[O:28]>C(Cl)(Cl)Cl.O>[CH3:18][C:16]1([CH3:17])[C@H:14]2[CH2:13][O:12][CH2:11][C@@H:10]([C:4]3[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=3)[N:15]2[C:27](=[O:28])[C:26](=[O:30])[O:19]1

参加物

6

反応物 3

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 673733842-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]propane-2-ol

生成物 1

HCID 67373385(6R,9aR)-1,1-dimethyl-6-(3,4,5-trifluorophenyl)tetrahydro [1,4]oxazino[3,4-c][1,4]oxazine-3,4-dione

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

To a solution of 2-[(3R,5R)-5-(3,4,5-trifluorophenyl)morpholine-3-yl]propane-2-ol (330 mg) and pyridine (2 mL) in chloroform (10 mL) was dropwise added oxalyl chloride (205 μL) while cooling with ice. The resultant solution was stirred at the same temperature for 1 hour, and then stirred for another 2 hours at room temperature. The resultant solution was diluted with water, and the organic layer was partitioned. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. Solvent was removed by distillation under reduced pressure. The resultant residue was purified by silica gel column chromatography (heptane/ethyl acetate), to thereby obtain the titled compound (260 mg). The physical properties of this crude product were as follows.

後処理

  1. temperaturewhile cooling with ice
  2. customthe organic layer was partitioned
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customSolvent was removed by distillation under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-4fd20f8db3314aaea9b31d5fcab683e4
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

反応ノート

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