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

HRID 20011

Reaction equation

[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]

Participants

Conditions

Temperature: 23 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-97b820d84b6847df95d2262091e04ca6
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745484B2

Linked notes

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