Sodium hydride → HCID 131734716, Verbindung

To a solution under N2 of trimethylsulfoxonium iodide (3.89 g, 17.7 mmol, 2 eq.) in DMSO (10 mL) cooled at r.t. with a water bath, sodium hydride 60% dispersion in mineral oil (707 mg, 17.7 mmol, 2 eq.) was added portionwise over 10 min. The resulting mixture was stirred at r.t. for 1 hour. A solution of (E)-N-methoxy-N-methyl-3-(pyridin-2-yl)acrylamide (1.70 g, 8.8 mmol, 1 eq.) in DMSO (5 mL) was added and the reaction mixture was stirred at r.t. for 18 hours. The reaction mixture was poured in sat. aq. NH4Cl soln. (50 mL) and extracted with DCM (3×50 mL). The comb. org. phases were washed with sat. aq. NaCl soln. (1×50 mL), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane+20% AcOEt to Heptane+80% AcOEt) to yield (±)-(trans)-2-pyridin-2-yl-cyclopropanecarboxylic acid methoxy-methyl-amide as an yellow oil.

1. stirringthe reaction mixture was stirred at r.t. for 18 hours
2. extraction(50 mL) and extracted with DCM (3×50 mL)
3. washphases were washed with sat. aq. NaCl soln
4. dry with material(1×50 mL), dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flashmaster (column: 100 g, flow: 45 mL/min, 30 fractions of 45 mL, Heptane+20% AcOEt to Heptane+80% AcOEt)

ORD-Eintrag

ord-adc58ceab3e44661a730c53bcb5e2824

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09255090B2