1-hydroxycyclopentane-1-carbonitrile

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

Procedure: 8-Methyl-6,9-diaza-spiro[4.5]decane-9-carboxylic acid tert-butyl ester was synthesized in analogy to 8,8-Dimethyl-6,9-diaza-spiro[4.5]decane-9-carboxylic acid tert-butyl ester starting from 1,2-diamino-propane and 1-hydroxycyclopentane-1-carbonitrile.

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

Procedure: To a solution of 6.1 ml of 1,2-diamino-2-methylpropane in 17 ml water 5.7 ml of 1-hydroxycyclopentane-1-carbonitrile was slowly added. The reaction was kept at reflux for 48 h, and the cooled to r.t. The precipitated product was isolated by suction and washed with water. From the filtrate additional solid could be obtained. The combined solids were freeze-dried and 9.32 g (90%) of the title compound were obtained, which could be used in the next step without further purification. at reflux for 48 h The precipitated product was isolated by suction washed with water From the filtrate additional solid could be obtained The combined solids were freeze-dried

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

Procedure: 8-Methyl-6,9-diaza-spiro[4.5]decane-9-carboxylic acid tert-butyl ester was synthesized in analogy to 8,8-dimethyl-6,9-diaza-spiro[4.5]decane-9-carboxylic acid tert-butyl ester starting from 1,2-diamino-propane and 1-hydroxycyclopentane-1-carbonitrile.

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

Procedure: 6-Benzyl-8-methyl-6,9-diaza-spiro[4.5]decane was synthesized in analogy to 6-benzyl-8,8-dimethyl-6,9-diaza-spiro[4.5]decane starting from 1,2-diamino-propane and 1-hydroxycyclopentane-1-carbonitrile.

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

Procedure: To a solution of 6.1 ml of 1,2-diamino-2-methylpropane in 17 ml water 5.7 ml of 1-hydroxycyclopentane-1-carbonitrile was slowly added. The reaction was kept at reflux for 48 h, and the cooled to r.t. The precipitated product was isolated by suction and washed with water. From the filtrate additional solid could be obtained. The combined solids were freeze-dried and 9.32 g (90%) of the title compound were obtained, which could be used in the next step without further purification. at reflux for 48 h The precipitated product was isolated by suction washed with water From the filtrate additional solid could be obtained The combined solids were freeze-dried

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

Procedure: To a solution of 6.1 ml of 1,2-diamino-2-methylpropane in 17 ml water 5.7 ml of 1-hydroxycyclopentane-1-carbonitrile was slowly added. The reaction was kept at reflux for 48 h, and the cooled to r.t. The precipitated product was isolated by suction and washed with water. From the filtrate additional solid could be obtained. The combined solids were freeze-dried and 9.32 g (90%) of the title compound were obtained, which could be used in the next step without further purification. at reflux for 48 h The precipitated product was isolated by suction washed with water From the filtrate additional solid could be obtained The combined solids were freeze-dried

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

Procedure: Ethyl azidoacetate (2.58 g, 20 mmol) was dissolved in tert-butanol (15 mL), and 1-hydroxycyclopentanecarbonitrile (2.20 g, 20 mmol) was added. A solution of sodium ascorbate (0.792 g, 4 mmol) in water (10 mL) followed by a 0.3 M solution of copper sulfate (0.67 mL) was added to the mixture, and stirring continued at room temperature for a further 48 hours. The solution was evaporated to dryness in vacuo and the residue was dissolved in EtOAc (50 mL), dried (MgSO4), filtered and evaporated in vacuo to afford the title compound as green-yellow crystals in 98% yield, 4.69 g. MS m/z 238 [M−H]− was added to the mixture The solution was evaporated to dryness in vacuo the residue was dissolved in EtOAc (50 mL) dried (MgSO4) filtered evaporated in vacuo