1-OXA-5-AZASPIRO[2.4]HEPTANE-5-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER Chemical Properties

storage temp. 

Sealed in dry,Store in freezer, under -20°C

form 

liquid

color 

Light yellow

Safety Information

Hazard Codes 

T

Risk Statements 

52

WGK Germany 

3

HS Code 

2934999090

1-OXA-5-AZASPIRO[2.4]HEPTANE-5-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER Usage And Synthesis

Uses

tert-butyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate is ureful reactant for the synthesis of spirocyclic-?3,?4-?dihydro-?2H-?benzo[b]?[1,?4]?oxazine derivatives.

Synthesis

At room temperature, tert-butyl 3-methylene pyrrolidine-1-carboxylate (195 mg, 1.06 mmol) was dissolved in dichloromethane (5 mL), followed by the addition of m-chloroperoxybenzoic acid (mCPBA, 275 mg, 1.60 mmol). The reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution (2 mL) and then the organic phase was extracted with ethyl acetate (60 mL). The organic phase was washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by fast silica gel column chromatography with the eluent being a hexane solution of 25% ethyl acetate to afford tert-butyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate (150 mg, 0.753 mmol, 71% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.91-3.42 (m, 3H), 3.48-3.16 (m, 1H), 2.93 (s, 2H), 2.35-2.17 (m, 1H), 1.93-1.79 (m, 1H), 1.47 (s, 9H).

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 21, p. 9738 - 9755
[2] Patent: WO2015/35278, 2015, A1. Location in patent: Page/Page column 89
[3] Patent: US2017/233339, 2017, A1

1-OXA-5-AZASPIRO[2.4]HEPTANE-5-CARBOXYLIC ACID, 1,1-DIMETHYLETHYL ESTER(301226-25-5)Related Product Information

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