ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Cesium carbonate → (R)-4-(4-benzyloxyphenyl)-2-methylpiperazine-1-carboxylic acid benzyl ester

HRID 2172235
ノート
印刷プレビュー

反応式

HRID 2172235 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][C@H:12]1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][C:29](Br)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:27][CH:28]=2)[CH2:13][C@H:12]1[CH3:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=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

9

反応物 4

HCID 10796Cesium carbonateHCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 40424346(R)-benzyl 2-methylpiperazine-1-carboxylateHCID 44558591Tri-t-butylphosphine fluoroborate

生成物 1

HCID 70873580(R)-4-(4-benzyloxyphenyl)-2-methylpiperazine-1-carboxylic acid benzyl ester収率 79%

試薬・触媒・溶媒 4

HCID 167845
palladium(II) acetate
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
95 °C

実験手順

(R)-2-Methylpiperazine-1-carboxylic acid benzyl ester (4.42 g, 18.9 mmol), 1-benzyloxy-4-bromobenzene (5.95 g, 22.6 mmol), cesium carbonate (8.60 g, 26.4 mmol) and toluene (49 ml) were mixed, and the atmosphere was replaced with nitrogen. Palladium acetate (0.42 g, 1.9 mmol) and tri-tert-butylphosphine tetrafluoroborate (0.66 g, 2.3 mmol) were added thereto and stirred at 90 to 100° C. for 2 days. Water and ethyl acetate were added to the reaction mixture, the mixture was filtered through Celite to remove insoluble matter. The filtrate was separated into layers. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→70:30) to afford the title compound as a brown oil (6.18 g, 79%).

後処理

  1. filtrationthe mixture was filtered through Celite
  2. customto remove insoluble matter
  3. customThe filtrate was separated into layers
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→70:30)

出典と根拠

ORDレコード
ord-a1f16b1433cc4bb28ba66ed5e97417c0
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09051333B2

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