methyl piperidine-2-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Piperidenemethanol was made from methyl pipecolinate as described in Method B1b. The 2-hydroxyethylamine was converted to 2-chloromethylpiperidinium chloride according to Method B7a. 2-Methyl4-nitrophenyl isothiocyanate was reacted with 2-chloromethylpiperidinium chloride according according to Method C1a to give 9-(2-methyl-4-nitrophenylimino)-1-aza-8-thiabicyclo[4.3.0]nonane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Piperidenemethanol was made from methyl pipecolinate as described in Method B1b. The 2-hydroxyethylamine was converted to 2-chloromethylpiperidinium chloride according to Method B7a. 2-Methyl4-nitrophenyl isothiocyanate was reacted with 2-chloromethylpiperidinium chloride according according to Method C1a to give 9-(2-methyl-4-nitrophenylimino)-1-aza-8-thiabicyclo[4.3.0]nonane.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl piperidine-2-carboxylate (5.2 g, 36.92 mmol) while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes) to yield the title compound (2.95 g, 99% yield) as a yellow oil. [M+H] calc'd for C14H17N3O6, 324. found, 324. The viscous yellow reaction was heated to 90° C. for one h to cool back to room temperature purified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes)