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

HRID 39160
ノート
印刷プレビュー

反応式

HRID 39160 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-530dd23ccee5450fb2d116346c40c697
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524767B2

反応ノート

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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