Trifluoroacetic acid → Benzyl 1,6-diazaspiro[3.5]nonane-1-carboxylate

HRID 1912403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912403
C(OC([N:8]1[CH2:26][CH2:25][CH2:24][C:10]2([N:13]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[CH2:12][CH2:11]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([N:13]1[C:10]2([CH2:24][CH2:25][CH2:26][NH:8][CH2:9]2)[CH2:11][CH2:12]1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 582933361-Benzyl 6-(tert-butyl) 1,6-diazaspiro[3.5]nonane-1,6-dicarboxylate

Produkt 1

HCID 58293362Benzyl 1,6-diazaspiro[3.5]nonane-1-carboxylateAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of an optically-active compound of 1,6-diazaspiro[3,5]-nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester (5.35 g) in chloroform (134 ml) cooled to 0° C. was added trifluoroacetic acid (27 ml), and the mixture was stirred for 30 minutes, warmed to room temperature and stirred for additional 30 minutes. The reaction mixture was cooled to 0° C., and thereto was added 4M aqueous sodium hydroxide solution (91 ml). The aqueous layer was extracted with chloroform (100 ml, 50 ml) twice, and the combined organic layer was washed with saturated aqueous sodium chloride solution and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1 to 4/1) to give the titled compound (2.37 g).

Aufarbeitung

  1. stirringstirred for additional 30 minutes
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. extractionThe aqueous layer was extracted with chloroform (100 ml, 50 ml) twice
  4. washthe combined organic layer was washed with saturated aqueous sodium chloride solution
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1 to 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-8d3626b262c140a89b70d7b10a22d4f5
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609647B2

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