tert-butyl 6-azido-2-azaspiro[3.3]heptane-2-carboxylate synthesis
- Product Name:tert-butyl 6-azido-2-azaspiro[3.3]heptane-2-carboxylate
- CAS Number:1239320-12-7
- Molecular formula:C11H18N4O2
- Molecular Weight:238.29
![tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2-carboxylate](/CAS/20200401/GIF/1239320-11-6.gif)
1239320-11-6
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Yield:1239320-12-7 500 mg
Reaction Conditions:
with Caswell No. 744A;benzo-15-crown-5 in N,N-dimethyl-formamide at 70;
Steps:
26 tert-Butyl 6-azido-2-azaspiro[3.3]heptane-2-carboxylate (26.3)
A mixture of tert-butyl 6-((methylsulfonyl)oxy)-2-azaspiro[3.3]heptane-2- carboxylate (26.2) (700 mg, crude), NaN3 (456 mg, 7.02 mmol) and 15-crown-5 (50 mg) in DMF (10 mL) was stirred at 70 °C overnight. TLC showed the reaction was complete. The reaction mixture was cooled to room temperature and partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to afford tert-butyl 6- azido-2-azaspiro[3.3]heptane-2-carboxylate (26.3) (500 mg, 90%, 2 steps) as a yellow oil.
References:
WO2016/90079,2016,A1 Location in patent:Paragraph 00491
![tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate](/CAS2/GIF/1147557-97-8.gif)
1147557-97-8
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![tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate](/CAS2/GIF/1181816-12-5.gif)
1181816-12-5
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