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

Lithium borohydride → 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide

HRID 640613
ノート
印刷プレビュー

反応式

HRID 640613 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:25]=[CH:24][C:19]([C:20](OC)=[O:21])=[C:18]([Br:26])[CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[Li+].[BH4-]>C1COCC1.CCOCC.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([C:13]([NH:15][C:16]4[CH:25]=[CH:24][C:19]([CH2:20][OH:21])=[C:18]([Br:26])[CH:17]=4)=[O:14])[CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]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

4

反応物 2

HCID 4148881Lithium borohydrideHCID 59207086Methyl 4-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-bromobenzoate

生成物 1

HCID 592062471-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide収率 74%

試薬・触媒・溶媒 1

HCID 70417672THF ether H2O溶媒

反応条件

温度
25 °C

実験手順

Methyl 4-(1-(benzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2-bromobenzoate (4.12 g, 9.9 mmol) was added to a solution of LiBH4 (429 mg, 19.8 mmol) in THF/ether/H2O (20/20/1 mL) and was allowed to stir at 25° C. After 16 hours, the reaction was quenched with H2O (10 mL). The reaction mixture was diluted with dichloromethane (25 mL) and was extracted with 1N HCl (30 mL×3) and brine (30 mL). The organic extracts were dried over Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes) to afford 1-(benzo[d][1,3]dioxol-5-yl)-N-(3-bromo-4-(hydroxymethyl)phenyl)cyclopropanecarboxamide (2.84 g, 74%); ESI-MS m/z calc. 389.0, found 390.1 (M+1)+; retention time 2.91 minutes.

後処理

  1. customthe reaction was quenched with H2O (10 mL)
  2. additionThe reaction mixture was diluted with dichloromethane (25 mL)
  3. extractionwas extracted with 1N HCl (30 mL×3) and brine (30 mL)
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. customevaporated
  6. customThe crude product was purified by chromatography on silica gel (eluting with 0-100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-35c97e870d8d4661bf983812cb4d823c
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07691902B2

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