Sodium hydride → HCID 67378655, Verbindung

HRID 1182663Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182663
[H-].[Na+].[CH3:3][N:4]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]2[C:5]1=[N:6][C@@H:7]1[CH2:16][CH2:15][CH2:14][C@@H:8]12.C1(C)C=CC(S([CH2:26][N+:27]#[C-:28])(=O)=O)=CC=1>C1COCC1>[CH3:3][N:4]1[C:12](=[O:13])[C:11]2=[CH:26][NH:27][CH:28]=[C:10]2[N:9]2[C@H:8]3[CH2:14][CH2:15][CH2:16][C@H:7]3[N:6]=[C:5]12

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 67379018(3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one

Produkt 1

HCID 67378655HCID 67378655, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Sodium hydride (95%, 112 mg, 4.44 mmol) is suspended in 3 mL of anhydrous THF, and then a mixture of (3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one (283 mg, 1.48 mmol) and p-toluenesulfonylmethyl isocyanide (97%, 347 mg, 1.77 mmol) in 5 mL of anhydrous THF is added dropwise. The mixture is stirred at room temperature for an hour, and then quenched with water. The mixture is extracted with CH2Cl2 (5×10 mL). The combined organic phase is washed with brine, and then dried with anhydrous Na2SO4. After filtration, the filtrate is evaporated to dryness under reduced pressure to give crude product (320 mg, yield 94%) as brown solids, which is used for the next reaction without further purification. MS (ESI) m/z 231.1 [M+H]+.

Aufarbeitung

  1. additionis added dropwise
  2. customquenched with water
  3. extractionThe mixture is extracted with CH2Cl2 (5×10 mL)
  4. washThe combined organic phase is washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationAfter filtration
  7. customthe filtrate is evaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8b3379aba6824c2ba9d4af5816ce3efc
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664207B2

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