تفاعل #88521

معادلة التفاعل

piperidin-4-ol

oxetanone

sodium triacetoxyborohydride

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title compound

المردود 60.4%

1-Oxetan-3-yl-piperidin-4-ol

المردود 60.4%

المذيبات

DCE

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 20 hours at ambient temperature
2. 2
   غسيلwas washed with methanol

الإجراء التجريبي

To a suspension of piperidin-4-ol (364 mg, 3.6 mmol) in DCE (30 mL) was added oxetanone (216 mg, 3.0 mmol). After 2 hours, sodium triacetoxyborohydride (1.02 g, 4.8 mmol) was added in one portion. After 20 hours at ambient temperature, the reaction mixture was loaded directly onto a 20 g SCX-2 cartridge which was washed with methanol, then 2N ammonia in methanol. Concentration of the combined basic fractions in-vacuo followed by flash chromatography of the resultant residue (silica, 10 g column, Si-SPE, 0-10% methanol in dichloromethane) afforded the title compound as a colourless oil (285 mg, 52%). 1H NMR (300 MHz, CDCl3): 4.64-4.63 (m, 4H), 3.77-3.77 (m, 1H), 3.49-3.47 (m, 1H), 2.65-2.55 (m, 2H), 2.04 (t, J=10.5 Hz, 2H), 1.94-1.93 (m, 2H), 1.62-1.61 (m, 2H), 1.47 (d, J=4.5 Hz, 1H).

المصدر