Cesium carbonate → (S)-tert-butyl 2-((4-nitro-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

HRID 522629

반응식

HRID 522629 반응식
CS(O[CH2:6][C@H:7]1[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)(=O)=O.[N+:20]([C:23]1[CH:24]=[N:25][NH:26][CH:27]=1)([O-:22])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[N+:20]([C:23]1[CH:24]=[N:25][N:26]([CH2:6][C@H:7]2[O:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:8]2)[CH:27]=1)([O-:22])=[O:21]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 86673567(S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate

생성물 1

HCID 118023401(S)-tert-butyl 2-((4-nitro-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate수율 107.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
55 °C

실험 절차

To a solution of (S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate (2.8 g, 9.5 mmol) and 4-nitro-1H-pyrazole (715 mg, 6.3 mmol) in acetonitrile (100 mL) was added cesium carbonate (6.2 g, 19.0 mmol). The reaction mixture was stirred at 55° C. overnight and then concentrated. The residue was dissolved in ethyl acetate (100 mL), washed with water (50 mL), dried over sodium sulfate, filtered and concentrated. The crude sample was purified by silica gel chromatography, eluting with petroleum ether:ethyl acetate=8:1, to afford (S)-tert-butyl 2-((4-nitro-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate as a yellow oil (2.12 g, 71%). MS (ES+) C13H20N4O5 requires: 312, found: 257 [M+H-56]+.

후처리

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with water (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude sample was purified by silica gel chromatography
  8. washeluting with petroleum ether

출처 및 근거

ORD 기록
ord-569ae0dfd35e4a7a8fd5e1dd96f9ab2f
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334263B2

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