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Cesium carbonate → tert-Butyl (3S)-3-(4-quinolylamino)pyrrolidine-1-carboxylate

HRID 333938
ノート
印刷プレビュー

反応式

HRID 333938 の反応式
C([O-])([O-])=O.[Cs+].[Cs+].[NH2:7][C@@H:8]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]1.Cl[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][CH:22]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([NH:7][C@H:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:22][CH:23]=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

6

反応物 3

HCID 10796Cesium carbonateHCID 691404-ChloroquinolineHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

生成物 1

HCID 86691593tert-Butyl (3S)-3-(4-quinolylamino)pyrrolidine-1-carboxylate収率 68%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒
HCID 31275
1,4-Dioxane
溶媒
2 回

反応条件

温度
100 °C

実験手順

A 5 ml vial was charged with Cs2CO3 (654 mg, 3.3 mmol) and was dried in vacuo at 60° C. for two hours. Palladium acetate (31.5 mg, 0.14 mmol), BI NAP (43 mg, 0.07 mmol) were added followed by anhydrous dioxane (2 ml). The mixture was sonicated for one hour after which tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate (186.3 mg, 1.0 mmol) and 4-chloroquinoline (163 mg, 1 mmol) dissolved in 2 ml anhydrous dioxane were added. The mixture was stirred at 100° C. overnight. The reaction mixture was purified directly by column chromatography (prepacked silica column, gradient heptan/ethyl acetate). 231 mg (0.68 mmol, 68%) of a solid were obtained. MS (APCI): m/z=314.0 [M+1]+.

後処理

  1. customwas dried in vacuo at 60° C. for two hours
  2. additionwere added
  3. customThe reaction mixture was purified directly by column chromatography (prepacked silica column, gradient heptan/ethyl acetate)

出典と根拠

ORDレコード
ord-a24aa5fe9eaa4b65af6674a29b9e4e5d
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08883791B2

反応ノート

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