Lithium Hexamethyldisilazide → HCID 44196480, compound

Participants

Reaction Conditions

Reaction Steps

To a flame dried round bottomed flask under nitrogen was added 250 mg (1.07 mmol) 6-Ethyl-3-nitro-2-phenyl-2,3,4,5-tetrahydro-pyridine as a mixture of cis and trans isomers and 5 ml of anhydrous THF (TLC rf.=Trans 0.6; Cis 0.4; eluting solvent hexane:ethylacetate/50:50). The reaction mixture was cooled to −78° C. and 1.07 ml (1.07 mmol) of 1N lithium bis(trimethylsilyl)amide solution in THF was introduced. The reaction mixture was stirred for 20 min, and then quenched directly into a well stirred solution of 2 gm Baker Silica Gel (40 uM Flash Chromatography Packing). The solids were filtered and the filtrate was concentrated in vacuo to afford an orange red oil, 0.23 gm (92%) as the desired cis isomer, Cis-6-Ethyl-3-nitro-2-phenyl-2,3,4,5-tetrahydro-pyridine (TLC rf.=0.4, hexane:ethylacetate/50:50). Mass spectrum APCI (m/z) 233 (p+1).

Provenance & Evidence