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Acetic Acid → 4-isopropyl-N-[4-((S)-1-ethyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide

HRID 2262642
ノート
印刷プレビュー

反応式

HRID 2262642 の反応式
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][NH:22][CH2:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:25](O)(=O)[CH3:26].C(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([C@@H:20]3[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21]3)=[CH:16][CH:15]=2)(=[O:11])=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]
参加物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 176Acetic AcidHCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 574700744-Isopropyl-N-((S)-4-pyrrolidin-3-yl-phenyl)-benzenesulfonamide

生成物 1

HCID 536286964-isopropyl-N-[4-((S)-1-ethyl-pyrrolidin-3-yl)-phenyl]-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

0.3 g of 4-Isopropyl-N—((S)-4-pyrrolidin-3-yl-phenyl)-benzenesulfonamide (0.87 mmol) were dissolved in 20 ml dichloromethane. After addition of 0.07 ml of acetic acid, 0.073 ml of acetaldehyde (1.31 mmol) and 0.277 g of sodium triacetoxyborohydride (1.31 mmol), the reaction mixture was stirred at room temperature for 30 minutes. The solvent was evaporated, the residue dissolved in water and the pH adjusted to pH 8-9 with aqueous sodium hydroxide solution. The aqueous phase was extracted three times with diethyl ether, the combined organic phases dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified via silica gel chromatography (chromabond column) with dichloromethane, dichloromethane/methanol 4% as eluent to yield 64 mg of the title compound.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in water
  3. extractionThe aqueous phase was extracted three times with diethyl ether
  4. dry with materialthe combined organic phases dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified via silica gel chromatography (chromabond column) with dichloromethane, dichloromethane/methanol 4% as eluent

出典と根拠

ORDレコード
ord-21307163eb5f4b92bee19dffa49351cf
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07851463B2

反応ノート

読み込み中…

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