Sodium Azide → (S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate

HRID 451729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451729
CS(O[CH2:6][C@@H:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C.CCOC(C)=O.O>[N:23]([CH2:6][C@@H:7]([NH:15][C:16](=[O:17])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[N+:24]=[N-:25]

Komponenten

6

Edukt 2

HCID 33557Sodium AzideHCID 10735550(S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate

Produkt 1

HCID 59382971(S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of (S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate (23.3 g, 0.070 mol) in anhydrous DMF (300 mL) was added solid NaN3 (13.5 g, 0.21 mol). The reaction mixture was heated at 80° C. overnight. After cooling to rt, the reaction solution was diluted with EtOAc (1200 mL) and water (400 mL). The organic phase was separated and washed with brine (3×300 mL), dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel to give (S)-tert-butyl 1-azido-3-cyclohexylpropan-2-ylcarbamate as a clear oil (13.6 g, 69%). 1H NMR (400 MHz, CDCl3): 4.45 (d, J=8.0 Hz, 1H), 3.84 (m, 1H), 3.45 (m, 1H), 3.31 (m, 1H), 1.81-1.60 (m, 5H), 1.45 (s, 9H), 1.40-0.78 (m, 8H). MS (E/Z): 383 (M+H+).

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. customThe organic phase was separated
  3. washwashed with brine (3×300 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-220e099d6d5c47df9d6b85d249de44dd
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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