methyl 6-nitrohexanoate

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

Procedure: 2-Nitrocyclohexanone (6.77 g; 47.3 mmol) was dissolved in dried MeOH (150 mL) and a two fold excess by weight of Amberlyst® A21 (13.5 g) was added. The mixture was refluxed under nitrogen for 1.5 h then filtered and evaporated to give 6-nitrohexanoic acid methyl ester (7.72 g; 42 mmol). Yield: 89%. a two fold excess by weight of Amberlyst® A21 (13.5 g) was added The mixture was refluxed under nitrogen for 1.5 h then filtered evaporated

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

Procedure: Commercially available 2-nitrocyclohexanone was refluxed in MeOH in presence of Amberlyst A21 to give 6-nitrohexanoic acid methyl ester 1. Reaction of 1 with N,N′-dibenzylethylenediamine diacetate and paraformaldehyde gave diazepine 2 which was firstly hydrogenated to 3 and then alkylated with t-butyl bromoacetate to give pentaester 4. Selective hydrolysis of 4 by means of LiOH in THF/H2O gave 5. Overall yield 13%.

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

Procedure: 2-Nitrocyclohexanone (6.77 g; 47.3 mmol) was dissolved in dried MeOH (150 mL) and a two fold excess by weight of Amberlyst® A21 (13.5 g) was added. The mixture was refluxed under nitrogen for 1.5 h then filtered and evaporated to give 6-nitrohexanoic acid methyl ester (7.72 g; 42 mmol). Yield: 89%. a two fold excess by weight of Amberlyst® A21 (13.5 g) was added The mixture was refluxed under nitrogen for 1.5 h then filtered evaporated