4-Morpholinecarbonyl chloride → 2-(4-Methoxy-benzyl)-8-[(3S,4S)-1-(morpholine-4-carbonyl)-4-phenyl-pyrrolidin-3-ylmethyl]-2,8-diaza-spiro[4.5]decan-1-one Hydrochloride

HRID 1182171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182171
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:22][NH:21][CH2:20]4)[CH2:14][CH2:13]3)[C:9]2=[O:30])=[CH:5][CH:4]=1.[N:33]1([C:39]([Cl:41])=[O:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[ClH:41].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([CH2:18][C@@H:19]4[C@@H:23]([C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH2:22][N:21]([C:39]([N:33]5[CH2:38][CH2:37][O:36][CH2:35][CH2:34]5)=[O:40])[CH2:20]4)[CH2:14][CH2:13]3)[C:9]2=[O:30])=[CH:31][CH:32]=1

Komponenten

5

Edukt 3

HCID 848104-Morpholinecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 114646642-(4-Methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one

Produkt 1

HCID 673689292-(4-Methoxy-benzyl)-8-[(3S,4S)-1-(morpholine-4-carbonyl)-4-phenyl-pyrrolidin-3-ylmethyl]-2,8-diaza-spiro[4.5]decan-1-one HydrochlorideAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-methoxy-benzyl)-8-((3R,4S)-4-phenyl-pyrrolidin-3-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one (60 μmol) in anhydrous DCM (1 mL) was added 4-morpholinecarbonyl chloride (21 μL, 180 μmol). The reaction mixture was stirred overnight at room temperature. Saturated sodium bicarbonate aqueous solution was added to the reaction mixture and the aqueous layer washed with DCM (3×2 mL). The organic layer was then concentrated in vacuo and purified by semi-preparative HPLC (Method D) and lyophilized to give Compound 157 as a colorless solid (6.2 mg, 19%).

Aufarbeitung

  1. washthe aqueous layer washed with DCM (3×2 mL)
  2. concentrationThe organic layer was then concentrated in vacuo
  3. custompurified by semi-preparative HPLC (Method D)

Quellen und Nachweise

ORD-Eintrag
ord-379697b093c24876be6871dbfc5ac4d5
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07288548B2

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