tert-butyl N-[1-(hydroxymethyl)cyclobutyl]carbamate

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 15 ml round-bottomed flask, 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid ethyl ester (180 mg, 0.74 mmol) was dissolved in THF (4 ml). The colorless solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 0.78 ml, 0.78 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h then sodium sulfate decahydrate was carefully added. When gas evolution has ceased, the ice bath was removed, sodium sulfate was added and the mixture was stirred for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate/methanol. The filtrate was concentrated to give (1-hydroxymethyl-cyclobutyl)-carbamic acid tert-butyl ester as an off-white waxy solid which was used without further purification. the ice bath was removed sodium sulfate was added the mixture was stirred for 30 min at room temperature The suspension was filtered over Celite rinsed with ethyl acetate/methanol The filtrate was concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 15 ml round-bottomed flask, 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid ethyl ester (180 mg, 0.74 mmol) was dissolved in THF (4 ml). The colorless solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 0.78 ml, 0.78 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h then sodium sulfate decahydrate was carefully added. When gas evolution has ceased, the ice bath was removed, sodium sulfate was added and the mixture was stirred for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate/methanol. The filtrate was concentrated to give (1-hydroxymethyl-cyclobutyl)-carbamic acid tert-butyl ester as an off-white waxy solid which was used without further purification. the ice bath was removed sodium sulfate was added the mixture was stirred for 30 min at room temperature The suspension was filtered over Celite rinsed with ethyl acetate/methanol The filtrate was concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 15 ml round-bottomed flask, 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid ethyl ester (180 mg, 0.74 mmol) was dissolved in THF (4 ml). The colorless solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 0.78 ml, 0.78 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h then sodium sulfate decahydrate was carefully added. When gas evolution has ceased, the ice bath was removed, sodium sulfate was added and the mixture was stirred for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate/methanol. The filtrate was concentrated to give (1-hydroxymethyl-cyclobutyl)-carbamic acid tert-butyl ester as an off-white waxy solid which was used without further purification. the ice bath was removed sodium sulfate was added the mixture was stirred for 30 min at room temperature The suspension was filtered over Celite rinsed with ethyl acetate/methanol The filtrate was concentrated

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

Procedure: (1-{5-[1-(4-Chloro-2-trifluoromethylbenzyl)-1H-indazol-5-ylmethylene]-2,4-dioxothiazolidin-3-ylmethyl}cyclobutyl)carbamic acid tert-butyl ester was prepared from 5-[1-(4-chloro-2-trifluoromethylbenzyl)-1H-indazol-5-ylmethylene]thiazolidine-2,4-dione (from Example 1) and (1-hydroxymethylcyclobutyl)carbamic acid tert-butyl ester following General Procedure J.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 15 ml round-bottomed flask, 1-tert-butoxycarbonylamino-cyclobutanecarboxylic acid ethyl ester (180 mg, 0.74 mmol) was dissolved in THF (4 ml). The colorless solution was cooled to 0° C. and lithium aluminum hydride (1.0 M in THF, 0.78 ml, 0.78 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 1.5 h then sodium sulfate decahydrate was carefully added. When gas evolution has ceased, the ice bath was removed, sodium sulfate was added and the mixture was stirred for 30 min at room temperature. The suspension was filtered over Celite and rinsed with ethyl acetate/methanol. The filtrate was concentrated to give (1-hydroxymethyl-cyclobutyl)-carbamic acid tert-butyl ester as an off-white waxy solid which was used without further purification. the ice bath was removed sodium sulfate was added the mixture was stirred for 30 min at room temperature The suspension was filtered over Celite rinsed with ethyl acetate/methanol The filtrate was concentrated