Реакция #67713

Уравнение реакции

Ammonium acetate

sodium cyanoborohydride

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

sodium carbonate

→

title compound

Выход 44.4%

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

Выход 44.4%

Растворители

methanol

Ethyl acetate

Условия реакции

Обработка

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

Методика

(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)+.

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