Cyclohexanone, 4,4-dimethyl- → Methyl(2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylate

HRID 1361297Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1361297
[C:1]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:18][C:19]1([CH3:26])[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1.C([O-])(O)=O.[Na+]>ClCCCl>[CH3:17][O:16][C:14]([C@@H:9]1[CH2:10][C@H:11]([NH:13][CH:22]2[CH2:23][CH2:24][C:19]([CH3:26])([CH3:18])[CH2:20][CH2:21]2)[CH2:12][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])=[O:15]

Komponenten

5

Edukt 3

HCID 138166Cyclohexanone, 4,4-dimethyl-HCID 516892Sodium BicarbonateHCID 5200425(2S,4S)-1-Tert-butyl 2-methyl 4-aminopyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 66970872Methyl(2S,4S)-1-BOC-4-[(4,4-dimethylcyclohexyl)amino]pyrrolidine-2-carboxylateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To methyl (2S,4S)-1-Boc-4-aminopyrrolidine-2-carboxylate (1.07 g, 4.38 mmol) and dimethylcyclohexanone (0.66 g, 5.25 mmol) in DCE (20 mL) was added dropwise NaBH(OAc) (1.39 g, 6.57 mmol) at rt. The reaction mixture was stirred at rt for 4 h, a saturated NaHCO3 aqueous solution was added, and extracted with DCM (50 mL×2) and EtOAc. The organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The obtained residue was purified by column chromatography (eluent, EtOAc/Hex=1/2) to give the title compound (1.16 g, 75%).

Aufarbeitung

  1. extractionextracted with DCM (50 mL×2) and EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by column chromatography (eluent, EtOAc/Hex=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-0ccbc25c64664fd1a98688cf38a9efac
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879852B2

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