Methanol → HCID 16206167, compound

Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate (2.7 g, 10 mmol) was dissolved in dry toluene (30 ml). The stirred solution was cooled to -63° C. under an atmosphere of N2, whereafter a solution of diisobutylaluminiumhydrid (DIBAH, 1 M, 20 ml) was added dropwise. Stirring was continued at -70° C. for 11/2 h, whereafter methanol (5 ml) was added, in order to destroy excess of DIBAH. At ambient temperature water (50 ml) was added, and the mixture was filtered through a pad of filter aid. The organic phase was dried over Na2SO4 and evaporated to leave an oily residue. Treatment with ether afforded precipitation of the side product 4-hydroxymethyl-1-methyl-4-phenylpiperidine as pale crystals. Filtration followed by evaporation of the filtrate left the title compound as an oil, which was processed without further purification.

1. additionwas added dropwise
2. customwas continued at -70° C. for 11
3. custom2 h
4. customto destroy excess of DIBAH
5. additionAt ambient temperature water (50 ml) was added
6. filtrationthe mixture was filtered through a pad of filter aid
7. dry with materialThe organic phase was dried over Na2SO4
8. customevaporated
9. customto leave an oily residue
10. customprecipitation of the side product 4-hydroxymethyl-1-methyl-4-phenylpiperidine as pale crystals
11. filtrationFiltration
12. customfollowed by evaporation of the filtrate
13. waitleft the title compound as an oil, which
14. customwas processed without further purification

ORD record

ord-251a148b674745cbaee378de4c9fd76e

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04845095