Cesium fluoride → HCID 90204320, compound

HRID 1480309Notes

Reaction equation

HRID 1480309 reaction equation
[CH3:1][C:2]([S:5](/[N:7]=[CH:8]/[C:9]1([CH3:13])[CH2:12][O:11][CH2:10]1)=[O:6])([CH3:4])[CH3:3].[F-].[Cs+].C[Si]([C:20]#[N:21])(C)C>C1COCC1>[C:20]([CH:8]([C:9]1([CH3:13])[CH2:12][O:11][CH2:10]1)[NH:7][S:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[O:6])#[N:21]

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 82115Trimethylsilyl cyanideHCID 90203770HCID 90203770, compound

Product 1

HCID 90204320HCID 90204320, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (NE)-2-methyl-N-[(3-methyloxetan-3-yl)methylene]propane-2-sulfinamide (CAN 1450658-44-2, 1.3 g, 6.39 mmole) in dry THF (35 ml) under argon atmosphere was added cesium fluoride (1.17 g, 7.67 mmol) followed by trimethylsilyl cyanide (761 mg, 1.03 ml, 7.67 mmol). The reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated in vacuo followed by dilution with ethylacetate. The organic phase was extracted with water and brine. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (1.21 g, 82%). MS (ESI, m/z): 231.6 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionThe organic phase was extracted with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated down to dryness
  5. customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-b41dca8078244ef185d9a963b95b934e
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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