Sodium bis(2-methoxyethoxy)aluminiumhydride → 5-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]

HRID 83986

反応式

HRID 83986 の反応式
CS([N:5]1[C:27]2[C:22](=[CH:23][C:24]([Cl:28])=[CH:25][CH:26]=2)[C:7]2([CH2:11][CH2:10][N:9]([CH2:12]/[CH:13]=[CH:14]/[C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[CH2:8]2)[CH2:6]1)(=O)=O.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>C1(C)C=CC=CC=1>[Cl:28][C:24]1[CH:23]=[C:22]2[C:7]3([CH2:11][CH2:10][N:9]([CH2:12]/[CH:13]=[CH:14]/[C:15]4[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=4)[CH2:8]3)[CH2:6][NH:5][C:27]2=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 689242391-Methanesulfonyl-5-chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]

生成物 1

HCID 689306495-Chloro-1'-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3'-pyrrolidine]収率 74.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

A solution of 1-methanesulfonyl-5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] obtained in Step D (256 mg) in toluene (25 ml) under argon was treated with sodium bis(2-methoxyethoxy)aluminium hydride (Red-Al, 65% in toluene, 0.67 ml) and the reaction mixture was stirred at 100° C. for 1 hour, cooled to room temperature, quenched by addition of ethyl acetate (10 ml), stirred for 15 min and concentrated in vacuo. The residue was purified by silica gel chromatography (eluent ethyl acetate:methanol 95:5) to afford 5-chloro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,3′-pyrrolidine] (157 mg) as a yellow oil, which was characterised by its mass and NMR spectra.

後処理

  1. temperaturecooled to room temperature
  2. customquenched by addition of ethyl acetate (10 ml)
  3. stirringstirred for 15 min
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (eluent ethyl acetate:methanol 95:5)

出典と根拠

ORDレコード
ord-8798f0c9457348929512f941c499cc49
出典データセット
uspto-grants-2014_09
特許番号
US08846907B2

関連ノート

読み込み中…