Triethylamine → 3-Ethyl 2-(phenylmethyl) 8-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-azaspiro[4.5]decane-2,3-dicarboxylate

HRID 454425Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 454425
[CH3:1][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][CH:7]1[CH2:21][CH2:20][C:10]2([CH2:14][NH:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11]2)[CH2:9][CH2:8]1)([CH3:4])[CH3:3].C(N(CC)CC)C.[CH:31]1[CH:36]=[CH:35][C:34]([CH2:37][O:38][C:39](Cl)=[O:40])=[CH:33][CH:32]=1>C(Cl)Cl>[CH3:1][C:2]([Si:5]([CH3:23])([CH3:22])[O:6][CH:7]1[CH2:21][CH2:20][C:10]2([CH2:14][N:13]([C:39]([O:38][CH2:37][C:34]3[CH:35]=[CH:36][CH:31]=[CH:32][CH:33]=3)=[O:40])[CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11]2)[CH2:9][CH2:8]1)([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 58313070HCID 58313070, Verbindung

Produkt 1

HCID 583131673-Ethyl 2-(phenylmethyl) 8-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-azaspiro[4.5]decane-2,3-dicarboxylateAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of ethyl 8-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-azaspiro[4.5]decane-3-carboxylate (110) (10.61 g, 31.3 mmol) dissolved in dry DCM, triethylamine was added (10.8 mL, 78 mmol), cooled to 0° C. followed by the addition of Cbz-Cl (6.2 mL, 43.5 mmol), and the reaction stirred at 0° C., for 5 min, rt for 1 h. Reaction diluted with DCM (700 mL), washed with 0.1N HCl (700 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 10-60% hexanes/EtOAc to afford the title compound as a yellow oil (5.73 g, 39% yield).

Aufarbeitung

  1. customReaction
  2. washwashed with 0.1N HCl (700 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 10-60% hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-d5a6bb1256b1440fa39239c6f98dc1b4
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492554B2

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