Ammonia → 2H-Pyran-3-acetic acid, 3-aminotetrahydro-, ethyl ester

Temperature

150 °C

Ethyl (2Z)-dihydro-2H-pyran-3(4H)-ylideneacetate (Preparation 37, 1.21 g, 7.11 mmol) was stirred in 1,4-dioxane (7 mL) in a microwave vial. A solution of 7M ammonia in methanol (5 mL) was added and the reaction heated for 3 hours at 150° C. in a Biotage Initiator™ microwave. A further solution of 7M ammonia in methanol (2 mL) was added and the reaction heated again for 2 hours at 150° C. in the microwave. The reaction was concentrated in vacuo and the residue dissolved in a further portion of 7M ammonia in methanol (10 mL) and heated for a further 5 hours at 150° C. in the microwave. The reaction was concentrated in vacuo to afford the title compound along with the methyl ester where trans-esterification had occurred. The material was used without further purification in the next step.

1. temperaturethe reaction heated again for 2 hours at 150° C. in the microwave
2. concentrationThe reaction was concentrated in vacuo
3. dissolutionthe residue dissolved in a further portion of 7M ammonia in methanol (10 mL)
4. temperatureheated for a further 5 hours at 150° C. in the microwave
5. concentrationThe reaction was concentrated in vacuo

ORD record

ord-2151be9f41ed4790a9cd90954504704e

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079878B2