1-(1-aminocyclobutyl)propan-2-ol

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

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

Procedure: A stirred solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (2.45 g, 9.27 mmol), Ac2O (5.30 mL, 56.1 mmol) and triethyl orthoformate (3.10 mL, 18.6 mmol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. To 1-[1-aminocyclobutyl]-2-propanol (1.20 g, 9.29 mmol) in anhydrous toluene (10 mL) was slowly added to a mixture of the residue in anhydrous toluene (30 mL) at 0° C. and stirred at room temperature for 2 hours. The solvent was removed by evaporation. Flash chromatography (AcOEt:Hexane=1:1) of the residue gave the title compound as a pale yellow solid (3.10 g, 83%). 1H-NMR (400 MHz, CDCl3) δ 0.95 (0.6H, t, J=7.3 Hz), 1.09 (2.4H, t, J=7.3 Hz), 1.29 (3H, d, J=6.1 Hz), 1.51 (1H, brs), 1.83-2.05 (4H, m), 2.18-2.35 (3H, m), 2.41-2.53 (1H, m), 3.95-4.15 (3H, m), 6.96-7.13 (1H, m), 8.27 (0.8H, d, J=14.7 Hz), 8.31 (0.2H, d, J=14.7 Hz), 10.30 (0.2H, d, J=13.4 Hz), 11.56 (0.8H, d, J=13.4 Hz). The mixture was concentrated in vacuo dried under high vacuum The solvent was removed by evaporation

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

Procedure: 10% Pd—C (300 mg) was added to a solution of 1-[1-(benzylamino)cyclobutyl]-2-propanol (2.24 g, 10.2 mmol) in EtOH (50 mL) and the mixture was stirred under H2 gas (5 kgf/cm2) at room temperature for 10 hours. The mixture was filtered and the filtrate was concentrated in vacuo. Distillation of the residue gave the title compound as a pale yellow oil (1.24 g, 94%). The mixture was filtered the filtrate was concentrated in vacuo Distillation of the residue

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

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

Procedure: A stirred solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (2.45 g, 9.27 mmol), Ac2O (5.30 mL, 56.1 mmol) and triethyl orthoformate (3.10 mL, 18.6 mmol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. To 1-[1-aminocyclobutyl]-2-propanol (1.20 g, 9.29 mmol) in anhydrous toluene (10 mL) was slowly added to a mixture of the residue in anhydrous toluene (30 mL) at 0° C. and stirred at room temperature for 2 hours. The solvent was removed by evaporation. Flash chromatography (AcOEt:Hexane=1:1) of the residue gave the title compound as a pale yellow solid (3.10 g, 83%). 1H-NMR (400 MHz, CDCl3) δ 0.95 (0.6H, t, J=7.3 Hz), 1.09 (2.4H, t, J=7.3 Hz), 1.29 (3H, d, J=6.1 Hz), 1.51 (1H, brs), 1.83-2.05 (4H, m), 2.18-2.35 (3H, m), 2.41-2.53 (1H, m), 3.95-4.15 (3H, m), 6.96-7.13 (1H, m), 8.27 (0.8H, d, J=14.7 Hz), 8.31 (0.2H, d, J=14.7 Hz), 10.30 (0.2H, d, J=13.4 Hz), 11.56 (0.8H, d, J=13.4 Hz). The mixture was concentrated in vacuo dried under high vacuum The solvent was removed by evaporation

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

Procedure: 10% Pd—C (300 mg) was added to a solution of 1-[1-(benzylamino)cyclobutyl]-2-propanol (2.24 g, 10.2 mmol) in EtOH (50 mL) and the mixture was stirred under H2 gas (5 kgf/cm2) at room temperature for 10 hours. The mixture was filtered and the filtrate was concentrated in vacuo. Distillation of the residue gave the title compound as a pale yellow oil (1.24 g, 94%). The mixture was filtered the filtrate was concentrated in vacuo Distillation of the residue

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

Procedure: A stirred solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (2.45 g, 9.27 mmol), Ac2O (5.30 mL, 56.1 mmol) and triethyl orthoformate (3.10 mL, 18.6 mmol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. To 1-[1-aminocyclobutyl]-2-propanol (1.20 g, 9.29 mmol) in anhydrous toluene (10 mL) was slowly added to a mixture of the residue in anhydrous toluene (30 mL) at 0° C. and stirred at room temperature for 2 hours. The solvent was removed by evaporation. Flash chromatography (AcOEt:Hexane=1:1) of the residue gave the title compound as a pale yellow solid (3.10 g, 83%). 1H-NMR (400 MHz, CDCl3) δ 0.95 (0.6H, t, J=7.3 Hz), 1.09 (2.4H, t, J=7.3 Hz), 1.29 (3H, d, J=6.1 Hz), 1.51 (1H, brs), 1.83-2.05 (4H, m), 2.18-2.35 (3H, m), 2.41-2.53 (1H, m), 3.95-4.15 (3H, m), 6.96-7.13 (1H, m), 8.27 (0.8H, d, J=14.7 Hz), 8.31 (0.2H, d, J=14.7 Hz), 10.30 (0.2H, d, J=13.4 Hz), 11.56 (0.8H, d, J=13.4 Hz). The mixture was concentrated in vacuo dried under high vacuum The solvent was removed by evaporation

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

Procedure: 10% Pd—C (300 mg) was added to a solution of 1-[1-(benzylamino)cyclobutyl]-2-propanol (2.24 g, 10.2 mmol) in EtOH (50 mL) and the mixture was stirred under H2 gas (5 kgf/cm2) at room temperature for 10 hours. The mixture was filtered and the filtrate was concentrated in vacuo. Distillation of the residue gave the title compound as a pale yellow oil (1.24 g, 94%). The mixture was filtered the filtrate was concentrated in vacuo Distillation of the residue