Reaktion #305604

Reaktionsgleichung

(S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate

NaN3

→

tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate

Ausbeute 64.0%

Lösungsmittel

EtOAc

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with H2O (3×20 mL)
2. 2
   Trocknendried over anhydrous Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe resulted slurry was purified through flash chromatography on silica gel (eluted with gradient system: 0-30% EtOAc in hexane)

Vorschrift

The solution of (S)-2-(tert-butoxycarbonylamino)-3-((R)-tetrahydro-2H-pyran-3-yl)propyl 4-methylbenzenesulfonate (132 mg, 0.32 mmol) and NaN3 (62 mg, 0.95 mmol) in anhydrous DMF was heated to 80° C. under N2 atmosphere for 1.5 hr, cooled to rt and diluted with EtOAc, and washed with H2O (3×20 mL), followed by brine, and dried over anhydrous Na2SO4, and filtered, and concentrated under reduced pressure. The resulted slurry was purified through flash chromatography on silica gel (eluted with gradient system: 0-30% EtOAc in hexane) to afford tert-butyl (S)-1-azido-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate 58 mg, yield 64%. MS ESI+ve m/z 307 (M+Na).

Quelle