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Hydrochloric Acid → methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate

HRID 421965
ノート
印刷プレビュー

反応式

HRID 421965 の反応式
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:29]([O:31][CH3:32])=[O:30])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([C:21](OC)=[O:22])[CH2:18][C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[BH4-].O.Cl>C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:29]([O:31][CH3:32])=[O:30])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([CH2:21][OH:22])[CH2:18][C:17]4[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]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 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 58765149dimethyl 13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate

生成物 1

HCID 16072734methyl 13-cyclohexyl-6-(hydroxymethyl)-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-10-carboxylate収率 85%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
0 °C

実験手順

Dimethyl 13-cyclohexyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate (prepared according to International patent application publication WO 2006/020082) was dissolved in anhydrous THF (0.02 M) and after cooling at 0° C. BH3THF complex (1.5 eq.) was added followed by LiBH4 (1 eq.) and water (4 eq.). The mixture was left stirring at RT for 2h, then 1N hydrochloric acid was slowly added. The crude was extracted twice with EtOAc, dried over Na2SO4, filtered, and all volatiles were removed in vacuo to obtain desired compound as a yellow solid (85%) that was used in the next step without purification. (ES+) m/z 404 (M+H)+.

後処理

  1. additionBH3THF complex (1.5 eq.) was added
  2. waitThe mixture was left
  3. extractionThe crude was extracted twice with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customall volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-1b52f181c0f9412180590557b9e1ceaa
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08101595B2

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