Lithium Hydroxide → N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamide

HRID 1969656Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969656
[N:1]([CH:4]1[CH:8]([CH3:9])[CH2:7][CH:6]([NH:10][S:11]([CH:14]2[CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH2:5]1)=C=O.[Li+].[OH-]>C1COCC1>[NH2:1][CH:4]1[CH:8]([CH3:9])[CH2:7][CH:6]([NH:10][S:11]([CH:14]2[CH2:15][CH2:16]2)(=[O:13])=[O:12])[CH2:5]1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 86660440N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide

Produkt 1

HCID 67216953N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamideAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of N-(3-isocyanato-4-methylcyclopentyl)cyclopropanesulfonamide (1.00 g, 4.09 mmol, Preparation #NNN.1) in THF (2.0 mL) was added aqueous LiOH (4 N, 20.5 mL, 82 mmol). The reaction was heated to about 50° C. for about 16 h, cooled to ambient temperature and partitioned between water (5 mL) and EtOAc (10 mL). The organic portion was separated and the aqueous portion was extracted with DCM (3×20 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give crude N-(3-amino-4-methylcyclopentyl)cyclopropanesulfonamide (0.66 g, 74%) as a white solid: LC/MS (Table 1, Method n) Rt=0.020 min; MS m/z: 219 (M+H)+.

Aufarbeitung

  1. temperaturecooled to ambient temperature
  2. custompartitioned between water (5 mL) and EtOAc (10 mL)
  3. customThe organic portion was separated
  4. extractionthe aqueous portion was extracted with DCM (3×20 mL)
  5. dry with materialThe combined organic extracts were dried over anhydrous MgSO4
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-7b78a8d480674f17b1f50911b96620de
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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