Potassium Carbonate → (2S)-1-{N-[2-(thiomorpholin-4-ylmethyl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile

HRID 1015537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1015537
Cl.[N:2]1([CH2:8][C:9]23[CH2:17][CH:13]4[CH2:14][CH:15]([CH2:16]2)[C:11]([NH2:18])([CH2:12]4)[CH2:10]3)[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1.Cl[CH2:20][C:21]([N:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C:28]#[N:29])=[O:22].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOC(C)=O>[N:2]1([CH2:8][C:9]23[CH2:17][CH:13]4[CH2:12][C:11]([NH:18][CH2:20][C:21]([N:23]5[CH2:27][CH2:26][CH2:25][C@H:24]5[C:28]#[N:29])=[O:22])([CH2:10]2)[CH:15]([CH2:14]4)[CH2:16]3)[CH2:7][CH2:6][S:5][CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11073883(2S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrileHCID 866427431-(Thiomorpholin-4-ylmethyl) tricyclo[3.3.1.03,7]nonan-3-amine hydrochloride salt

Produkt 1

HCID 24853119(2S)-1-{N-[2-(thiomorpholin-4-ylmethyl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrileAusbeute 35,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of the hydrochloride salt (0.17 g, 0.51 mmol) obtained in step II above in DMSO (2.0 mL) at room temperature under nitrogen atmosphere was added (2S)-1-(chloroacetyl)pyrrolidine-2-carbonitrile (0.09 g, 0.52 mmol) and K2CO3 (0.35 g, 2.55 mmol. After stirring the reaction mixture for 3 h, it was diluted with EtOAc and washed with water and brine, dried over Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain (2S)-1-{N-[2-(thiomorpholin-4-ylmethyl)hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile as an off-white solid (0.07 g) in 35% yield. m/z (M+1) 389; 1H NMR (CDCl3) 300 MHz δ 4.83-4.75 (m, 1H), 3.90-3.45 (m, 4H), 2.85-2.70 (m, 4H), 2.70-2.60 (m, 4H), 2.48-2.35 (m, 2H), 2.35-2.15 (m, 4H), 2.0-1.75 (m, 4H), 1.68-1.40 (m, 5H), 1.38-1.25 (m, 1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8d028cab1d7c4ad1b9f4594a67f77f8c
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985759B2

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