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Methyltriphenylphosphonium iodide → (R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-5'-isopropenyl-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 1480006
ノート
印刷プレビュー

反応式

HRID 1480006 の反応式
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:28]([C:35]1[N:40]=[N:39][C:38]([N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[N:51][C:50]([C:53](=O)[CH3:54])=[CH:49][N:48]=3)[C@H:43]([CH3:56])[CH2:42]2)=[C:37]([CH3:57])[C:36]=1[CH3:58])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH2:28]([C:35]1[N:40]=[N:39][C:38]([N:41]2[CH2:46][CH2:45][N:44]([C:47]3[CH:52]=[N:51][C:50]([C:53]([CH3:2])=[CH2:54])=[CH:49][N:48]=3)[C@H:43]([CH3:56])[CH2:42]2)=[C:37]([CH3:57])[C:36]=1[CH3:58])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
参加物反応条件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 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxideHCID 451071751-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl]-ethanone

生成物 1

HCID 59191459(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-5'-isopropenyl-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl収率 37.3%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

反応条件

温度
5 °C

実験手順

Methyltriphenylphosphonium iodide (410 mg, 1.010 mmol) is added to THF (5.5 mL) and cooled to 5° C. Potassium tert-butoxide (1.1 mL, 1M in THF, 1.1 mmol) is added dropwise and the reaction is stirred for 30 min. 1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl]-ethanone (350 mg, 0.841 mmol) in THF (1.5 mL) is added to the reaction. The reaction is allowed to stir 1 h at 5° C., and then the ice bath is removed and the reaction is allowed to stir an additional 16 h at room temperature. Remove THF in vacuo. The residue is purified by flash chromatography on silica gel (60-90% EtOAc/heptane) to afford the title compound (130 mg, 37%).

後処理

  1. stirringto stir 1 h at 5° C.
  2. customthe ice bath is removed
  3. stirringto stir an additional 16 h at room temperature
  4. customThe residue is purified by flash chromatography on silica gel (60-90% EtOAc/heptane)

出典と根拠

ORDレコード
ord-a3b357ef1f0748fcbd7322330986b160
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409871B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート