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

HRID 20011

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HRID 20011 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
23 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-97b820d84b6847df95d2262091e04ca6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745484B2

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