Tetrabutylammonium Fluoride → (2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one

HRID 627160ノート

反応式

HRID 627160 の反応式
[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[CH:7]=[CH:8][C@H:9]2[CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:4][N:5]1[C:11](=[O:12])[N:10]2[CH2:13][C@H:6]1[CH:7]=[CH:8][C@H:9]2[CH2:14][OH:15])[CH:2]=[CH2:3]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 89851884(2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one2 回

生成物 1

HCID 89852367(2S,5R)-6-(allyloxy)-2-(hydroxymethyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of (2S,5R)-6-(allyloxy)-2-((tert-butyldimethylsilyloxy)methyl)-1,6-diazabicyclo[3.2.1]oct-3-en-7-one (Intermediate 129, 1.64 g, 5.05 mmol) in THF (40 mL), tetrabutylammonium fluoride (6.06 ml, 6.06 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 1 hr. The mixture was concentrated and purified by silica gel column (40 g, 50-100% Hex/EA) to give the desired product (1.03 g) as an yellow oil.

後処理

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel column (40 g, 50-100% Hex/EA)

出典と根拠

ORDレコード
ord-8142ed1dcc6a45a089fbc71a9af96d94
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

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