HCID 69050173, Verbindung → (S)-(4-cyclobutyl-1,4-diazepan-1-yl)(2-(3-fluorobenzyl)pyrrolidin-2-yl)methanone

HRID 882772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 882772
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([C:21]([N:23]1[CH2:29][CH2:28][CH2:27][N:26]([CH:30]2[CH2:33][CH2:32][CH2:31]2)[CH2:25][CH2:24]1)=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)=O)(C)(C)C>CCO.Cl.O1CCOCC1>[CH:30]1([N:26]2[CH2:27][CH2:28][CH2:29][N:23]([C:21]([C@@:9]3([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=4)[CH2:10][CH2:11][CH2:12][NH:8]3)=[O:22])[CH2:24][CH2:25]2)[CH2:31][CH2:32][CH2:33]1

Komponenten

5

Edukt 1

HCID 69050173HCID 69050173, Verbindung

Produkt 1

HCID 46887647(S)-(4-cyclobutyl-1,4-diazepan-1-yl)(2-(3-fluorobenzyl)pyrrolidin-2-yl)methanoneAusbeute 54,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-2-(3-fluoro-benzyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (40.0 mg) in EtOH (5.0 mL) and 4 M HCl in dioxane (2.0 mL) was stirred for 10 h. The mixture was concentrated and the residue diluted with CH2Cl2 and treated with Et3N. The mixture was washed with water and concentrated to yield title compound (17 mg, 54%). MS (ESI): mass calcd. for C26H38FN3O3, 359.60; m/z found, 360.3 [M+H]+. 1H NMR (CDCl3): 7.23-6.84 (m, 4H), 3.87-3.40 (m, 4H), 3.15-3.0 (m, 1H), 2.97-2.71 (m, 4H), 2.68-2.40 (m, 4H), 2.10-1.98 (m, 3H), 1.93-1.54 (m, 9H).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additionthe residue diluted with CH2Cl2
  3. additiontreated with Et3N
  4. washThe mixture was washed with water
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8b57c59b1d114c7182292ac91335a548
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236792B2

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