Dimethylformamide → tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 538735ノート

反応式

HRID 538735 の反応式
[CH:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=O.C#C.CC[N:19](CC)[CH2:20][CH3:21].C[N:25](C=O)C>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:25]1[CH:21]=[CH:20][N:19]=[C:1]1[C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 6326AcetyleneHCID 8471TriethylamineHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

生成物 1

HCID 49783269tert-Butyl (2S)-2-(1H-imidazol-2-yl)pyrrolidine-1-carboxylate収率 34%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
100 °C

実験手順

To a solution of 4 (0.78 g, 1.7 mmol), acetylene intermediate A5 (0.56 g, 1.7 mmol, synthesized as described in Scheme 1-1), CuI (63 mg, 0.33 mmol), and Et3N (0.67 mL, 5.0 mmol) in DMF (20 mL) was added Pd(PPh3)4 (0.19 g, 0.165 mmol). The resulting mixture was degassed with N2, and then stirred at 100° C. overnight in a sealed tube. The reaction mixture was slowly dropped into H2O (100 mL). The precipitate was collected and then dissolved in EtOAc. The organic phase was dried, filtered, and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (EtOAc) to afford 5 (420 mg, 34% yield). LC-MS (ESI): m/z 746.4 (M+H)+

後処理

  1. customThe resulting mixture was degassed with N2
  2. additionThe reaction mixture was slowly dropped into H2O (100 mL)
  3. customThe precipitate was collected
  4. dissolutiondissolved in EtOAc
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a residue, which
  9. customwas purified by silica gel column chromatography (EtOAc)

出典と根拠

ORDレコード
ord-a3a82204f86140158d54f4c1312aaad7
出典データセット
uspto-grants-2014_10
特許番号
US08865756B2

反応ノート

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