tert-butyl 4-aminocyclohexane-1-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-amino-cyclohexanecarboxylic acid tert-butyl ester (500 mg, 2.500 mmol) in MeOH (3 mL) is added TEA (140 uL, 1.000 mmol), MgSO4 (452 mg, 3.750 mmol), and benzaldehyde (278 uL, 2.750 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (568 mg, 15.00 mmol) is added portionwise over 10 min. The mixture stirs 1 h at ambient temperature. Then H2O (20 mL) is added and the mixture is extracted with EtOAc (2×50 mL), dried and concentrated to affords 730 mg of 4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 290, Rt=0.80 min (method 6). The mixture stirs 1 h at ambient temperature the mixture is extracted with EtOAc (2×50 mL) dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester (3.0 g, 9.009 mmol) in THF (80 mL) is added TEA (0.24 mL, 1.724 mmol) and 10% Pd/C (wet) (420 mg). The mixture stirs under a blanket of hydrogen gas at atmospheric pressure for 12 h. The mixture is then filtered though celite. The celite is washed with MeOH (50 mL). The filtrated is concentrated to afford 1.8 g of 4-amino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 200, Rt=0.39 min (method 6). The mixture is then filtered though celite The celite is washed with MeOH (50 mL) The filtrated is concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester (3.0 g, 9.009 mmol) in THF (80 mL) is added TEA (0.24 mL, 1.724 mmol) and 10% Pd/C (wet) (420 mg). The mixture stirs under a blanket of hydrogen gas at atmospheric pressure for 12 h. The mixture is then filtered though celite. The celite is washed with MeOH (50 mL). The filtrated is concentrated to afford 1.8 g of 4-amino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 200, Rt=0.39 min (method 6). The mixture is then filtered though celite The celite is washed with MeOH (50 mL) The filtrated is concentrated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-amino-cyclohexanecarboxylic acid tert-butyl ester (500 mg, 2.500 mmol) in MeOH (3 mL) is added TEA (140 uL, 1.000 mmol), MgSO4 (452 mg, 3.750 mmol), and benzaldehyde (278 uL, 2.750 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (568 mg, 15.00 mmol) is added portionwise over 10 min. The mixture stirs 1 h at ambient temperature. Then H2O (20 mL) is added and the mixture is extracted with EtOAc (2×50 mL), dried and concentrated to affords 730 mg of 4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 290, Rt=0.80 min (method 6). The mixture stirs 1 h at ambient temperature the mixture is extracted with EtOAc (2×50 mL) dried concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester (3.0 g, 9.009 mmol) in THF (80 mL) is added TEA (0.24 mL, 1.724 mmol) and 10% Pd/C (wet) (420 mg). The mixture stirs under a blanket of hydrogen gas at atmospheric pressure for 12 h. The mixture is then filtered though celite. The celite is washed with MeOH (50 mL). The filtrated is concentrated to afford 1.8 g of 4-amino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 200, Rt=0.39 min (method 6). The mixture is then filtered though celite The celite is washed with MeOH (50 mL) The filtrated is concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-benzyloxycarbonylamino-cyclohexanecarboxylic acid tert-butyl ester (3.0 g, 9.009 mmol) in THF (80 mL) is added TEA (0.24 mL, 1.724 mmol) and 10% Pd/C (wet) (420 mg). The mixture stirs under a blanket of hydrogen gas at atmospheric pressure for 12 h. The mixture is then filtered though celite. The celite is washed with MeOH (50 mL). The filtrated is concentrated to afford 1.8 g of 4-amino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 200, Rt=0.39 min (method 6). The mixture is then filtered though celite The celite is washed with MeOH (50 mL) The filtrated is concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (0.0088 mol) (example 4a) in acetonitrile is treated with tert-butyl 4-aminocyclohexanecarboxylate (0.026 mol). The reaction mixture is refluxed for about 3-4 hrs. Solvent is evaporated off and water is added and extraction is done with ethyl acetate. The organic layer is washed with brine, dried and concentrated under reduced pressure to give crude compound, which is purified by column chromatography. The reaction mixture is refluxed for about 3-4 hrs Solvent is evaporated off water is added extraction The organic layer is washed with brine dried concentrated under reduced pressure to give crude compound, which is purified by column chromatography

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 4-amino-cyclohexanecarboxylic acid tert-butyl ester (500 mg, 2.500 mmol) in MeOH (3 mL) is added TEA (140 uL, 1.000 mmol), MgSO4 (452 mg, 3.750 mmol), and benzaldehyde (278 uL, 2.750 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (568 mg, 15.00 mmol) is added portionwise over 10 min. The mixture stirs 1 h at ambient temperature. Then H2O (20 mL) is added and the mixture is extracted with EtOAc (2×50 mL), dried and concentrated to affords 730 mg of 4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 290, Rt=0.80 min (method 6). The mixture stirs 1 h at ambient temperature the mixture is extracted with EtOAc (2×50 mL) dried concentrated