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Diisopropylethylamine → 1,1-dimethylethyl (2S)-4-[(3-fluoro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 534744
ノート
印刷プレビュー

反応式

HRID 534744 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5]([F:12])[CH:4]=1.CCN(C(C)C)C(C)C.[CH3:22][C@H:23]1[CH2:28][NH:27][CH2:26][CH2:25][N:24]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C>[F:12][C:5]1[CH:4]=[C:3]([CH2:2][N:27]2[CH2:26][CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C@@H:23]([CH3:22])[CH2:28]2)[CH:8]=[CH:7][C:6]=1[N+:9]([O-:11])=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 27746613-Fluoro-4-nitrobenzyl bromideHCID 10081508tert-Butyl (2S)-2-methylpiperazine-1-carboxylate

生成物 1

HCID 592621851,1-dimethylethyl (2S)-4-[(3-fluoro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate収率 92.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 4-(bromomethyl)-2-fluoro-1-nitrobenzene (232 mg, 1 mmol) and Hunig's base (0.192 mL, 1.1 mmol) in DMF (3 mL) was treated with 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (200 mg, 1 mmol) in DMF (3 mL) and stirred at room temperature for 20 minutes. The reaction mixture was concentrated, re-dissolved in DCM and washed with water and brine, then dried and concentrated. The crude product was purified by column chromatography. Elution with EtOAc/pentane yielded the title compound as a colourless gum (327 mg). δH (CDCl3, 400 MHz) 8.03 (1H, m), 7.34 (1H, dd), 7.27 (1H, m), 4.22 (1H, br.s), 3.84 (1H, d), 3.58 (1H, d), 3.47 (1H, d), 3.13 (1H, td), 2.72 (1H, m), 2.54 (1H, m), 2.22 (1H, dd), 2.09 (1H, m), 1.46 (9H, s), 1.26 (3H, d) [values corrected for incorrectly referenced TMS at 0.62 ppm on spectrum].

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionre-dissolved in DCM
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washElution with EtOAc/pentane

出典と根拠

ORDレコード
ord-48993971b13a48aaa2c00c8ec0d8aa37
出典データセット
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08853218B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート