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4-Methylmorpholine → HCID 67211349、化合物

HRID 452137
ノート
印刷プレビュー

反応式

HRID 452137 の反応式
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:28]=[CH:27][C:13]3/[C:14](=C/C(O)=O)/[C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[CH2:17][CH2:18][C:12]=3[CH:11]=2)[C:7]2[CH:29]=[CH:30][CH:31]=[CH:32][C:6]=2[N:5]=1)[CH2:2][CH3:3].CN1CC[O:37][CH2:36][CH2:35]1.C(Cl)(=O)OCC(C)C.[BH4-].[Na+]>COCCOC.O>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:28]=[CH:27][C:13]3/[C:14](=[C:36](/[OH:37])\[CH3:35])/[C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[CH2:17][CH2:18][C:12]=3[CH:11]=2)[C:7]2[CH:29]=[CH:30][CH:31]=[CH:32][C:6]=2[N:5]=1)[CH2:2][CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 67211673HCID 67211673、化合物

生成物 1

HCID 67211349HCID 67211349、化合物収率 55.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回
HCID 8071
1,2-Dimethoxyethane
溶媒

実験手順

(E)-[2-(2-Propylbenzimidazol-1-yl)methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]acetic acid (80 mg, 0.189 mmol) obtained in Example 2 was dissolved in 1,2-dimethoxyethane (0.7 mL), N-methylmorpholine (62 μL, 0.567 mmol) and isobutyl chlorocarbonate (49 μL, 0.378 mmol) were added, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered, and the filtrate was added to a solution (0.6 mL) of sodium borohydride (36 mg, 0.945 mmol) in water at 0° C., and the mixture was stirred for 10 min. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=95/5) to give the title compound (compound 13) (43 mg, 55%).

後処理

  1. filtrationThe reaction mixture was filtered
  2. stirringthe mixture was stirred for 10 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=95/5)

出典と根拠

ORDレコード
ord-76dc073a0116482483f33c1eef30e71b
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08486980B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート