Methylamine → (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-(methylamino)propan-2-ylcarbamate

HRID 451760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451760
CS(O[CH2:6][C@@H:7]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8][C:9]1([F:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=O)=O.[CH3:24][NH2:25]>C(O)C>[F:15][C:9]1([CH2:8][C@H:7]([NH:16][C:17](=[O:18])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:6][NH:25][CH3:24])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 86639447(S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate

Produkt 1

HCID 68710746(S)-tert-butyl 1-(1-fluorocyclohexyl)-3-(methylamino)propan-2-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Crude (S)-2-(tert-butoxycarbonylamino)-3-(1-fluorocyclohexyl)propyl methanesulfonate and (n-Bu)4N+T (249 mg, 1.0 mmol) were dissolved in 33% methylamine in ethanol (50 mL). The mixture was heated to 50° C. for 17 h. The solution was cooled to rt and the volatile materials were removed in vacuo. The residue was dissolved in ether, washed with brine, dried over Na2SO4, filtered and evaporated. To afford crude (S)-tert-butyl 1-(1-fluorocyclohexyl)-3-(methylamino)propan-2-ylcarbamate.

Aufarbeitung

  1. temperatureThe solution was cooled to rt
  2. customthe volatile materials were removed in vacuo
  3. dissolutionThe residue was dissolved in ether
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-995d78ba016744d28f3160f21a1834c1
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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