Triethylamine → 1,4-Dioxa-10-azadispiro[4.2.4.2]tetradecan-9-one

Temperature

25 °C

To a stirred solution of 8-cyanomethyl-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (12 g, 47.3 mmol) in a mixture of NH3-EtOH (200 ml, 7:93) was added Raney-Ni (4.16 g, 70.95 mmol) under nitrogen atmosphere at 25° C. The reaction mixture was then hydrogenated at 40° C. in an autoclave under 400 psi H2 pressure for 16 h. After the completion of reaction, the mixture was filtered through a bed of celite, and the filtrate was evaporated under reduced pressure. The crude material thus obtained (10 g, 38.9 mmol) was dissolved in dry toluene (100 ml) and to the stirred solution was added Et3N (10 ml, 71.14 mmol) under a nitrogen atmosphere at 25° C. The mixture was then heated under reflux for 24 h. After the completion of reaction, it was cooled to 25° C., the precipitated white solid was filtered, washed with hexane (3×50 ml), dried under vacuum to give the title compound (7.3 g) as a white solid. MS (m/e): 212.2 [MH+].

1. customAfter the completion of reaction
2. filtrationthe mixture was filtered through a bed of celite
3. customthe filtrate was evaporated under reduced pressure
4. customThe crude material thus obtained (10 g, 38.9 mmol)
5. temperatureThe mixture was then heated
6. temperatureunder reflux for 24 h
7. customAfter the completion of reaction, it
8. filtrationthe precipitated white solid was filtered
9. washwashed with hexane (3×50 ml)
10. customdried under vacuum

ORD record

ord-4a4da0153503427fb88e1ad3d1ca3706

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703807B2