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Dimethylformamide → BOC-aminoether

HRID 1007574
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HRID 1007574 반응식
[C:1](OC(N1CCC(O)CC1)=O)([CH3:4])([CH3:3])[CH3:2].[C:15](=[O:18])([O-:17])[O-:16].[Cs+].[Cs+].C[N:22](C=O)C>FC1C=CC(C(F)(F)F)=CC=1>[C:15]([O:17][NH2:22])([O:16][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:18]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

생성물 1

HCID 11992149BOC-aminoether수율 81%

시약·촉매·용매 1

HCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-촉매

실험 절차

Part A: A solution of N-(tert-butyloxycarbonyl)-4-piperidinol (5.00 g, 2.48 mmol), 4-fluorobenzo-trifluoride (3.46 mL, 2.73 mmol), and cesium carbonate (12.1 g, 3.72 mmol) in DMF (60 mL) was heated at 120 degrees Celsius under an atmosphere of nitrogen for 2 days. The mixture was concentrated, diluted with H2O, and extracted with ethyl acetate. The organic layer was washed with H2O and brine, dried with MgSO4, and concentrated in vacuo. Chromatography (on silica, ethyl acetate/hexane) provided the BOC-aminoether as a white solid (6.97 g, 81%); Anal. calculated. for C17H22NO3F3: C, 59.12; H, 6.42; N, 4.06. Found: C, 59.29; H, 6.47; N, 3.99.

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후처리

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-564d61f4c66d43b5939e96b599eabb07
출처 데이터셋
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06794511B2

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