Methanol → {2-[(2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester

HRID 219495

Reaktionsgleichung

Reaktionsgleichung von HRID 219495
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][C:18]1([CH3:25])[O:22][CH:21]([CH2:23][NH2:24])[CH2:20][O:19]1.CO>C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([NH:24][CH2:23][CH:21]1[CH2:20][O:19][C:18]([CH3:25])([CH3:17])[O:22]1)[CH3:11])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 41223491,3-Dioxolane-4-methanamine, 2,2-dimethyl-HCID 114141093-((Tert-butoxycarbonyl)amino)propyl methanesulfonate

Produkt 1

HCID 68496101{2-[(2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl esterAusbeute 32,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The commercially available Tert-butyl-N-(2-hydroxypropyl)carbamate (10 g, 57.0 mmol)) and trietylamine (12 ml, 85.6 mmol) were dissolved in dichloromethane (60 mL) and cooled to 0° C. Methanesulfonyl chloride (4.9 ml, 62.7 mmol) was added dropwise to the ice-cold solution and the reaction was allowed to warm up to room temperature with stirring overnight. The reaction was then quenched with NaOH (1M, 5 ml). The organics were washed with water (2×100 ml) and then brine, collected, dried over MgSO4, filtered and evaporated under reduced pressure to give methanesulfonic acid 3-tert-butoxycarbonylamino-propyl ester (13.5 g). The crude methanesulfonic acid 3-tert-butoxycarbonylamino-propyl ester (13.5 g, 53 mmol) and 2,2-dimethyl-1,3-dioxolane-4-methanamine (12 g, 91.6 mmol) were stirred overnight at room temperature. The mixture was dissolved in ethyl acetate (100 ml) and washed with water (3×100 ml) and brine. The organics were collected, dried over MgSO4, filtered and evaporated under reduced pressure to give an oil. This was purified by silica column chromatography eluting with ethyl acetate: methanol to give the desired product {2-[(2,2-Dimethyl-[1,3]dioxolan-4-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester (4.74 g, 17.3 mmol). Mass Spec (ESI) m/z: [M+H]+=289.12. 1H NMR (CDCl3; 300 MHz) δ=5.15 (s, br, 1H), 4.19 (quin, 1H), 4.02 (t, 1H), 3.66 (t, 1H), 3.18 (q, 2H), 2.70 (m, 4H), 1.63 (quin, 2H), 1.42 (s, 9H), 1.40 (s, 3H), 1.40 (s, 3H). 13C NMR (CDCl3; 300 MHz) δ=156.00, 109.05, 78.85, 75.23, 67.47, 52.30, 47.91, 39.20, 29.69, 28.35, 26.81, 25.37.

Aufarbeitung

  1. washwashed with water (3×100 ml) and brine
  2. customThe organics were collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give an oil
  7. customThis was purified by silica column chromatography
  8. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-f5cea4b29d134f4a81a667882383030d
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202511B2

Verknüpfte Notizen

Wird geladen…