Tetrahydrofuran → HCID 22643288、化合物

HRID 2414846ノート

反応式

HRID 2414846 の反応式
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:26][O:25][C:16]3[CH:17]=[CH:18][C:19]4[N:20]=[C:21]([CH3:24])[O:22][C:23]=4[C:15]=3[O:14]2)(=O)=O)=CC=1.FC(F)(F)[C:29]1[CH:30]=[C:31]([C:35]2[CH2:36][CH2:37][NH:38][CH2:39][CH:40]=2)[CH:32]=[CH:33][CH:34]=1.C1COCC1.C(O)(=O)/C=C/C(O)=O>CN(C=O)C.C(O)C>[CH3:24][C:21]1[O:22][C:23]2=[C:15]3[C:16](=[CH:17][CH:18]=[C:19]2[N:20]=1)[O:25][CH2:26][CH:13]([CH2:12][N:38]1[CH2:37][CH:36]=[C:35]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:29][CH:30]=2)[CH2:40][CH2:39]1)[O:14]3

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 444972Fumaric AcidHCID 111280344-[3-(Trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridineHCID 11245807(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate

生成物 1

HCID 22643288HCID 22643288、化合物収率 20.1%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate (0.40 g, 1.1 mmole) and 4-(3-trifluoromethyl-phenyl)-1,2,3,6-tetrahydro-pyridine (0.35 g, 1.54 mmole) were combined in 5 mL of DMF and 5 ml of THF under nitrogen. This solution was refluxed under nitrogen for overnight. After completion, the reaction was cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuum. The resulting crude oil was column chromatographed on silica gel using first methylene chloride to remove impurities and then 1% methanol/methylene chloride to elute the (S)-enantiomer of the title compound. This was recrystallized from ethanol with the addition of one equivalent of fumaric acid to give 80 mg of white solid, m.p. 170-173° C.

後処理

  1. temperatureThis solution was refluxed under nitrogen for overnight
  2. custompartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuum
  6. customchromatographed on silica gel using first methylene chloride
  7. customto remove impurities
  8. wash1% methanol/methylene chloride to elute the (S)-enantiomer of the title compound

出典と根拠

ORDレコード
ord-8fecabd3a8fa4e1c8d246b92ebec0793
出典データセット
uspto-grants-2004_11
特許番号
US06815448B2

反応ノート

読み込み中…