반응 #67713

반응 방정식

Ammonium acetate

sodium cyanoborohydride

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

sodium carbonate

→

title compound

수율 44.4%

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

수율 44.4%

용매

methanol

Ethyl acetate

반응 조건

후처리

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

실험 절차

(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)+.

출처