1-(2-aminophenyl)cyclobutan-1-ol

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-(2-Aminophenyl)cyclobutanol (56 mg, 0.343 mmol), 2,4,5-trichloropyrimidine (40 μl, 0.349 mmol) and N,N-diisopropylethylamine (120 μl, 0.694 mmol) were suspended in 2-propanol (1.5 mL) in a sealed tube, and the solution was heated to 85° C. for 4 hours. The reaction mixture was partitioned between H2O (15 mL) and CH2Cl2 (3×15 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography (Analogix, 0 to 25% ethyl acetate-hexanes over 25 minutes, 4 g silica, 18 mL/minute) to give the title compound. The reaction mixture was partitioned between H2O (15 mL) and CH2Cl2 (3×15 mL) The combined organic layers were dried (Na2SO4) filtered concentrated The product was purified by flash chromatography (Analogix, 0 to 25% ethyl acetate-hexanes over 25 minutes, 4 g silica, 18 mL/minute)

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

Procedure: N-(2-(1-hydroxycyclobutyl)phenyl)formamide (103 mg, 0.539 mmol) and potassium hydroxide (0.015 mL, 0.539 mmol) were combined in methanol (3 mL) and the mixture was heated to reflux for 3 hours. The reaction mixture was diluted with H2O (25 mL) and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography (Analogix, 0 to 40% ethyl acetate in hexanes over 25 minutes, 4 g silica, 18 mL/minutes) to give 1-(2-aminophenyl)cyclobutanol. the mixture was heated to reflux for 3 hours extracted with ethyl acetate (3×25 mL) The combined organic layers were dried (Na2SO4) filtered concentrated The product was purified by flash chromatography (Analogix, 0 to 40% ethyl acetate in hexanes over 25 minutes, 4 g silica, 18 mL/minutes)