Diisopropylethylamine → Methyl 1-({5-[(diallylamino)methyl]thien-2-yl}sulfonyl)piperidine-4-carboxylate

HRID 906642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906642
[CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.[CH3:27][O:28][C:29](=[O:36])[CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>C(Cl)(Cl)Cl.C(Cl)Cl>[CH2:1]([N:4]([CH2:8][C:9]1[S:13][C:12]([S:14]([N:33]2[CH2:34][CH2:35][CH:30]([C:29]([O:28][CH3:27])=[O:36])[CH2:31][CH2:32]2)(=[O:16])=[O:15])=[CH:11][CH:10]=1)[CH2:5][CH:6]=[CH2:7])[CH:2]=[CH2:3]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 424914Methyl isonipecotateHCID 113807695-Diallylaminomethyl-thiophene-2-sulfonyl chloride

Produkt 1

HCID 67403857Methyl 1-({5-[(diallylamino)methyl]thien-2-yl}sulfonyl)piperidine-4-carboxylateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Diallylaminomethyl-thiophene-2-sulfonyl chloride 229b (270 mg, 1.88 mmol) and DIEA (0.88 mL, 5.13 mmol) were dissolved in 10 mL chloroform. This solution was added methylisonipecotate (269 mg, 1.88 mmol) in 1 mL chloroform. The reaction was stirred for 3 h, diluted with CH2Cl2 and extracted with HCl (0.1N), NaHCO3 sat. and brine. The organic layer was dried over MgSO4 and evaporated to dryness. The crude was purified by flash chromatography on silica gel using cyclohexane/EtOAc 1:1 as eluent to obtain 440 mg (65%) of 327a as colorless oil: H′ NMR (CDCl3) δ 7.30 (d, J=3.6 Hz, 1H), 6.83 (d, J=3.6 1H), 5.78 (m, 2H), 5.18 (m, 4H), 3.70 (s, 2H), 3.52 (m, 6H), 3.07 (m, 4H), 2.50 (m, 2H), 2.25 (m, 1H), 1.93 (m, 2H), 1.84 (m, 2H). M/Z APCI: 399.2 (M+1)

Aufarbeitung

  1. extractionextracted with HCl (0.1N), NaHCO3 sat. and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated to dryness
  4. customThe crude was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-dd04dffdbee14282b9faee6dc920e001
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012995B1

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