Diethyl Ether → (S)-N-((S)-1-((tert-butyldimethylsilyl)oxy)-4-cyclopropylbut-3-yn-2-yl)-2-methylpropane-2-sulfinamide

HRID 595976Notes

Reaction equation

C([Mg]Br)C.CCOCC.[C:10]([CH:12]1[CH2:14][CH2:13]1)#[CH:11].[Si:15]([O:22][CH2:23]/[CH:24]=[N:25]/[S@:26]([C:28]([CH3:31])([CH3:30])[CH3:29])=[O:27])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>C1COCC1.C(Cl)Cl>[Si:15]([O:22][CH2:23][C@@H:24]([NH:25][S@:26]([C:28]([CH3:31])([CH3:30])[CH3:29])=[O:27])[C:11]#[C:10][CH:12]1[CH2:14][CH2:13]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 50 °C

Procedure

3.0 M ethyl magnesium bromide in Et2O (0.360 mL, 1.081 mmol) was added to a solution of ethynylcyclopropane (71.5 mg, 1.081 mmol) in THF (4 mL). The solution was heated to 50° C. for 1 h, then the resulting Grignard was added to a −78° C. solution of (S,E)-N-(2-((tert-butyldimethylsilyl)oxy)ethylidene)-2-methylpropane-2-sulfinamide (100 mg, 0.360 mmol) in DCM (4.00 mL), and the reaction was allowed to warm to room temperature. After 3h, the reaction was quenched with sat. aq. NH4Cl. The layers were separated and the organics were dried over magnesium sulfate and concentrated to provide (S)—N—((S)-1-((tert-butyldimethylsilyl)oxy)-4-cyclopropylbut-3-yn-2-yl)-2-methylpropane-2-sulfinamide, which was used directly. LCMS (m/z): 344.1 (MH+), 1.23 min.

Workup

temperatureto warm to room temperature
customAfter 3h, the reaction was quenched with sat. aq. NH4Cl
customThe layers were separated
dry with materialthe organics were dried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-f275ab399e864d158216c771fd7daec1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242996B2

Reaction notes

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