Nitromethane → Ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate

To a stirred and cooled mixture of 85.5 parts of ethyl 4-oxo-1-piperidinecarboxylate, 33.6 parts of nitromethane and 240 parts of methanol were added dropwise 10 parts of a sodium methoxide solution 30% at 10°~15° C. Upon completion, stirring was continued first for 2 hours at about 10° C. and further overnight at room temperature. The reaction mixture was evaporated at room temperature, crushed ice was added to the oily residue and the whole was acidified with acetic acid. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The oily residue was solidified on triturating in petroleum ether. The product was filtered off and dried, yielding 73 parts of ethyl 4-hydroxy-4-(nitromethyl)-1-piperidinecarboxylate (intermediate 3).

1. temperaturecooled
2. stirringUpon completion, stirring
3. customThe reaction mixture was evaporated at room temperature
4. customcrushed ice
5. additionwas added to the oily residue
6. extractionThe product was extracted with trichloromethane
7. customThe extract was dried
8. filtrationfiltered
9. customevaporated
10. customon triturating in petroleum ether
11. filtrationThe product was filtered off
12. customdried

ORD record

ord-40216e3ef4e545b49a2565aab147c64e

Source dataset

uspto-grants-1988_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04749702