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

HRID 2194477
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HRID 2194477 반응식
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]>O1CCCC1>[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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

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 tetrahydrofuran (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 RT. 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).

후처리

  1. stirringStir for 1 hour at RT
  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

출처 및 근거

ORD 기록
ord-6c15153f4ced4f64aee210d2a6128428
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08334293B2

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