(S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester → (S)-2-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1839662

Reaktionsgleichung

Reaktionsgleichung von HRID 1839662
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23](Cl)=[O:24])=[O:17])([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][C@H:19]1[C:23]([N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[NH:1][CH:2]=[CH:3][C:4]1=2)=[O:24])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 11148997(S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 225617901,4,5,6,7,8-Hexahydropyrrolo[3,2-B]azepine

Produkt 1

HCID 20761536(S)-2-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (664 mg) in DCM (10 mL) at 0° C. was added oxalyl chloride (4.7 mmol), followed by one drop of DMF. After stirring at rt for 2 hours, the solvent was concentrated to give S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester. To a solution of 1,4,5,6,7,8-hexahydro-pyrrolo[3,2-b]azepine (350 mg, 2.6 mmol) was added TEA (362μL) and (S)-2-chlorocarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester (dissolved in 10 mL of DCM). After stirring at rt for overnight, the reaction was diluted with DCM, washed with NaHCO3, brine, dried and concentrated. The residue was purified on a silica gel column to give 410 mg of (S)-2-(5,6,7,8-tetrahydro-1H-pyrrolo[3,2-b]azepine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown liquid.

Aufarbeitung

  1. washwashed with NaHCO3, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-36d73ea88af54453b60d369c13af4b4d
Quelldatensatz
uspto-grants-2004_01
Patentnummer
US06677368B2

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