تفاعل #67713

معادلة التفاعل

Ammonium acetate

sodium cyanoborohydride

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

sodium carbonate

→

title compound

المردود 44.4%

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

المردود 44.4%

المذيبات

methanol

Ethyl acetate

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

(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)+.

المصدر