tert-butyl 6-azido-2-azaspiro[3.3]heptane-2-carboxylate synthesis

3synthesis methods

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

1239320-11-6
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tert-butyl 6-azido-2-azaspiro[3.3]heptane-2-carboxylate

1239320-12-7
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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

1147557-97-8 Synthesis

tert-butyl 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxylate

1147557-97-8
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$14.00/100mg

1239320-12-7
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References

1181816-12-5 Synthesis

tert-butyl 6-oxo-2-azaspiro[3.3]heptane-2-carboxylate

1181816-12-5
181 suppliers
$9.00/100mg

1239320-12-7
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References