Reaktion #67713

Reaktionsgleichung

Ammonium acetate

sodium cyanoborohydride

(4-Oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

sodium carbonate

→

title compound

Ausbeute 44.4%

(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

Ausbeute 44.4%

Lösungsmittel

methanol

Ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe organic layer was separated
2. 2
   Extraktionthe aqueous layer was extracted three times with ethyl acetate
3. 3
   TrocknenThe combined extracts were dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified with flash column chromatography on silica eluting with a gradient (dichloromethane/methanol/ammonia 100:0:0→140:10:1)

Vorschrift

(4-Oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (CAS 477584-38-6, 446 mg, 2.07 mmol) was dissolved in 20 mL methanol. Ammonium acetate (1.63 g, 21 mmol) and sodium cyanoborohydride (507 mg, 8.1 mmol) were added and the reaction mixture was stirred at room temperature for 2 days. Ethyl acetate and 2N sodium carbonate solution were added. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified with flash column chromatography on silica eluting with a gradient (dichloromethane/methanol/ammonia 100:0:0→140:10:1) to provide 199 mg (44%) of the title compound as a white solid. MS (m/e): 161.2 (M-butene)+.

Quelle