tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate synthesis
- Product Name:tert-Butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate
- CAS Number:478837-18-2
- Molecular formula:C12H21NO3
- Molecular Weight:227.3
185099-67-6
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Yield: 92%
Reaction Conditions:
with sodium tetrahydroborate;ethanol at 20; for 1 h;
Steps:
14.1
Sodium borohydride (178 mg, 4.7 mmol) was added to a solution of tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (0.50 g, 2.2 mmol) in ethanol (10 mL), and the resulting mixture was stirred at room temperature for one hour. The mixture was quenched with saturated ammonium chloride solution (30 mL), and extracted with ethyl acetate (3x 20 mL). The combined extract was washed with water then brine, dried over sodium sulfate, filtered and concentrated to give tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (463 mg, 92% yield) as a mixture of endo and exo stereoisomers. GC-MS (EI) for C12H21NO3: 227 (M+).
References:
EXELIXIS, INC.;AAY, Naing;BLAZEY, Charles, M.;BOWLES, Owen, Joseph;BUSSENIUS, Joerg;CURTIS, Jeffry, Kimo;DEFINA, Steven, Charles;DUBENKO, Larisa;HARRIS, Jason, R.;JACKSON-UGUETO, Eileen, E.;KIM, Angie, Inyoung;MANALO, Jean-claire, Limun;PACK, Michael;PETO, Csaba, J.;RICE, Kenneth, D.;TSANG, Tsze, H.;WANG, Longcheng WO2010/138490, 2010, A1 Location in patent:Page/Page column 33
![8-Azabicyclo[3.2.1]octan-3-ol](/CAS/20180601/GIF/7432-11-3.gif)
7432-11-3
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25602-68-0
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478837-18-2
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