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

HRID 522629

反応式

HRID 522629 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
55 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-569ae0dfd35e4a7a8fd5e1dd96f9ab2f
出典データセット
uspto-grants-2016_05
特許番号
US09334263B2

関連ノート

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