Sodium Hydroxide → (r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

HRID 545580ノート

反応式

HRID 545580 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH:19][C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([CH:25]=O)[CH:11]=2.Cl.[NH2:31][OH:32].[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:18]2[CH2:17][CH2:16][C@@H:15]([NH:19][C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:14][C:13]=2[C:12]2[C:7]1=[CH:8][CH:9]=[C:10]([CH:25]=[N:31][OH:32])[CH:11]=2

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 59161221(r)-Cyclopropanecarboxylic acid[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide

生成物 1

HCID 87305657(r)-Cyclopropanecarboxylic acid[9-(3-fluoro-benzyl)-6-(hydroxyimino-methyl)-2,3,4,9-tetrahydro-1h-carbazol-3-yl]-amide収率 82%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Combine (R)-cyclopropanecarboxylic acid[9-(3-fluorobenzyl)-6-formyl-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-amide (Preparation 71) (1.50 g, 3.82 mmol), hydroxylamine hydrochloride (0.801 g, 11.5 mmol), and sodium hydroxide (0.23 g, 5.76 mmol) and stir under nitrogen for 1.5 h. Dilute with water and extract with EtOAc. Pass the dark residue through a pad of silica eluting with 50% EtOAc/hexanes to give 1.27 g (82%) of the title compound. MS (ES): m/z 406 (M+1).

後処理

  1. extractionextract with EtOAc

出典と根拠

ORDレコード
ord-caddcfd136cd4178a3c77039e5c4a049
出典データセット
uspto-grants-2011_05
特許番号
US07935722B2

反応ノート

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