Potassium Carbonate → (2S)-1-{N-[2-[(1,1-dioxidoisothiazolidin-2-yl)methyl]hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile

HRID 1015541Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1015541
[O:1]=[S:2]1(=[O:18])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]12[CH2:16][CH:12]3[CH2:13][CH:14]([CH2:15]1)[C:10]([NH2:17])([CH2:11]3)[CH2:9]2.C([O-])([O-])=O.[K+].[K+].Cl[CH2:26][C:27]([N:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[C:34]#[N:35])=[O:28]>CS(C)=O.CCOC(C)=O>[O:1]=[S:2]1(=[O:18])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]12[CH2:16][CH:12]3[CH2:11][C:10]([NH:17][CH2:26][C:27]([N:29]4[CH2:33][CH2:32][CH2:31][C@H:30]4[C:34]#[N:35])=[O:28])([CH2:9]1)[CH:14]([CH2:13]3)[CH2:15]2

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11073883(2S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrileHCID 670178751-[(1,1-Dioxidoisothiazolidin-2-yl) methyl]tricyclo[3.3.1.03,7]nonan-3-amine

Produkt 1

HCID 24853120(2S)-1-{N-[2-[(1,1-dioxidoisothiazolidin-2-yl)methyl]hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrileAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred mixture of the amine obtained in step IV (0.26 g, 0.96 mmol) and K2CO3 (0.42 g, 2.9 mmol) in DMSO (4.0 mL) at ice bath temperature was added under nitrogen atmosphere (S)-1-(2-chloro-acetyl)pyrrolidine-2-carbonitrile (0.17 g, 1.0 mmol). After stirring the reaction mixture for 3 h at r.t, it was diluted with EtOAc, washed with water and brine, dried over Na2SO4, and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography to obtain (2S)-1-{N-[2-[(1,1-dioxidoisothiazolidin-2-yl)methyl]hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile as an off-white solid (0.17 g) in 43% yield. m/z (M+1) 407; 1H NMR (CDCl3) 300 MHz δ 4.87-4.76 (m, 1H), 3.70-3.40 (m, 2H), 3.44 (s, 2H), 3.32 (t, J=6.7 Hz, 2H), 3.10 (t, J=7.5 Hz, 2H), 2.93 (s, 2H), 2.41-2.10 (m, 8H), 1.90-1.46 (m, 7H), 1.43-1.35 (m, 1H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated under reduced pressure
  4. customThe crude product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f2be02d2398745ef93fa5a12691c2004
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985759B2

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