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4-Methylmorpholine → 1-[2-(4-Fluoro-3-trifluoromethyl-phenyl)-2-oxo-ethylcarbamoyl]-piperidine-4-carboxylic acid tert-butyl ester

HRID 419751
ノート
印刷プレビュー

反応式

HRID 419751 の反応式
CN1CCOCC1.C(O[C:13]([N:15]1[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]1)=[O:14])(C)(C)C.ClC(O[CH2:28][CH:29]([CH3:31])[CH3:30])=O.Cl.[NH2:33][CH2:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([F:43])=[C:39]([C:44]([F:47])([F:46])[F:45])[CH:38]=1)=[O:36]>C1COCC1>[C:29]([O:23][C:21]([CH:18]1[CH2:17][CH2:16][N:15]([C:13](=[O:14])[NH:33][CH2:34][C:35]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[C:39]([C:44]([F:47])([F:45])[F:46])[CH:38]=2)=[O:36])[CH2:20][CH2:19]1)=[O:22])([CH3:31])([CH3:30])[CH3:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 666499872-Amino-1-[4-fluoro-3-(trifluoromethyl)phenyl]ethanone Hydrochloride

生成物 1

HCID 666498871-[2-(4-Fluoro-3-trifluoromethyl-phenyl)-2-oxo-ethylcarbamoyl]-piperidine-4-carboxylic acid tert-butyl ester収率 70.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

Add N-methylmorpholine (3 equiv; 631.52 mmoles; 69.66 mL) to a solution of Piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (1.20 equiv; 252.61 mmoles; 57.92 g) in THF (400 mL). Cool the mixture to −10° C. with a dry ice-acetone bath. Add isobutyl chloroformate (1.1 equiv; 231.56 mmoles; 30.26 mL) dropwise while maintaining the temperature below −5° C. After 30 min at −5°−10° C., add 2-amino-1-(4-fluoro-3-trifluoromethyl-phenyl)-ethanone hydrochloride (54.23 g; 1.00 equiv; 210.51 mmoles) suspended in THF (300 mL) and stir the mixture in the bath at −5° C. for 20 min. Stir for 1 hour at room temperature. Add water and EtOAc, then wash the organic layer with water and saturated aqueous sodium chloride. Dry over MgSO4, filter and remove solvent in vacuo. Suspend the crude in MTBE and stir for 2 hours. Filter the solid and dry in vacuo to give 1-[2-(4-Fluoro-3-trifluoromethyl-phenyl)-2-oxo-ethylcarbamoyl]-piperidine-4-carboxylic acid tert-butyl ester (64.44 g; 70.79% yield).

後処理

  1. stirringStir for 1 hour at room temperature
  2. washAdd water and EtOAc, then wash the organic layer with water and saturated aqueous sodium chloride
  3. dry with materialDry over MgSO4
  4. filtrationfilter
  5. customremove solvent in vacuo
  6. stirringstir for 2 hours
  7. filtrationFilter the solid
  8. customdry in vacuo

出典と根拠

ORDレコード
ord-7c77cf5da3fe4051b6fd546b1ba670a3
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08093383B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート