Triethylamine → 2-(2-Chloro-4-cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1942217

Reaktionsgleichung

Reaktionsgleichung von HRID 1942217
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N:10]3[CH2:14][CH2:13][C:12]4([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4)[C:11]3=[O:20])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.S(Cl)([Cl:24])(=O)=O.CCN(CC)CC>C(Cl)(Cl)Cl>[Cl:24][C:6]1[CH:5]=[C:4]([CH:1]2[CH2:3][CH2:2]2)[CH:9]=[CH:8][C:7]=1[N:10]1[CH2:14][CH2:13][C:12]2([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[C:11]1=[O:20]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 582872772-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

Produkt 1

HCID 582872722-(2-Chloro-4-cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-oneAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 0.275 g (1 mmol) 2-(4-Cyclopropyl-phenyl)-2,8-diaza-spiro[4.5]decan-1-one. 1.57 g (11.3 mmol) sulfuryl chloride and 0.154 g (1.52 mmol) NEt3 in 50 mL CHCl3 was stirred at room temperature. After evaporation of the volatiles the residue was taken up in DMF and subjected to purification by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. The product containing fractions were evaporated to yield 94 mg (30%) of the title compound as light yellow gum. MS m/e: 305.1 [M+H]+.

Aufarbeitung

  1. customAfter evaporation of the volatiles the residue
  2. customsubjected to purification by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. additionThe product containing fractions
  6. customwere evaporated

Quellen und Nachweise

ORD-Eintrag
ord-87155c578a514598b98c3ac5dc7a05fa
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389539B2

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