Triethylsilanol → (NE,R)-N-[2-[1-[tert-butyl(dimethyl)silyl]oxycyclopropyl]ethylidene]-2-methylpropane-2-sulfinamide

HRID 1009106

反応式

HRID 1009106 の反応式
[Si:1]([O:8][C:9]1([CH2:12][CH:13]=O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](O)(CC)(CC)CC.[CH3:23][C:24]([S@:27]([NH2:29])=[O:28])([CH3:26])[CH3:25]>C(Cl)Cl>[Si:1]([O:8][C:9]1([CH2:12]/[CH:13]=[N:29]/[S@@:27]([C:24]([CH3:26])([CH3:25])[CH3:23])=[O:28])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 69005TriethylsilanolHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 866141192-{1-[(Tert-butyldimethylsilyl)oxy]cyclopropyl}acetaldehyde

生成物 1

HCID 87349123(NE,R)-N-[2-[1-[tert-butyl(dimethyl)silyl]oxycyclopropyl]ethylidene]-2-methylpropane-2-sulfinamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

To a 1.0 L round bottom flask containing 2-(1-(tert-butyldimethylsilyloxy)cyclopropyl)acetaldehyde (5.00 g, 23.3 mmol) (crude 10.5 g with TESOH, 1H NMR showed about 50/50 sm to impurity) was added DCM (200 mL) and the mixture was allowed to stir at 23° C. for 5 min. At this time, (R)-2-methylpropane-2-sulfinamide (2.83 g, 23.3 mmol) and cupric sulfate anhydrous (2.58 ml, 58.3 mmol) were added and the reaction was allowed to stir for 40 h. The copper salts were removed by celite filtration. The filtrate was concentrated to give a yellow oil that was purified on a 330 g Isco column (5 to 20% EtOAc in hexanes) to afford the title compound as a colorless oil.

後処理

  1. stirringto stir for 40 h
  2. customThe copper salts were removed by celite filtration
  3. concentrationThe filtrate was concentrated
  4. customto give a yellow oil that
  5. customwas purified on a 330 g Isco column (5 to 20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-e98deeed756841f9b628db108597f238
出典データセット
uspto-grants-2011_07
特許番号
US07973047B2

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