(2-methylcyclopentyl)methanol

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

Procedure: To a cold (-20°) stirred solution of 10.8 g. 1-hydroxymethyl-2-methylcyclopentane prepared by lithium aluminum hydride reduction of methyl 2-methylcyclopentanecarboxylate and 13.4 ml. triethylamine in 300 ml. ether is added dropwise 5.6 ml. methanesulfonyl chloride in 5 ml. of either. After addition is completed, the solution is warmed to room temperature, stirred for 30 minutes and filtered directly into a solution of 23.1 g. ethyl 4-aminophenyl acetate in 100 ml. ether. After 17 hours at room temperature, the precipitate is filtered and washed with several portions of methylene chloride. The organic solution is washed twice with 100 ml. water, 100 ml. brine, dried and evaporated. The tan residue is crystallized from ethanol and from acetonitrile to yield the title compound as white crystals. After addition stirred for 30 minutes filtered directly into a solution of 23.1 g the precipitate is filtered washed with several portions of methylene chloride The organic solution is washed twice with 100 ml brine, dried evaporated The tan residue is crystallized from ethanol and from acetonitrile

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

Procedure: To a cold (-20°) stirred solution of 10.8 g. 1-hydroxymethyl-2-methylcyclopentane prepared by lithium aluminum hydride reduction of methyl 2-methylcyclopentanecarboxylate and 13.4 ml. triethylamine in 300 ml. ether is added dropwise 5.6 ml. methanesulfonyl chloride in 5 ml. of either. After addition is completed, the solution is warmed to room temperature, stirred for 30 minutes and filtered directly into a solution of 23.1 g. ethyl 4-aminophenyl acetate in 100 ml. ether. After 17 hours at room temperature, the precipitate is filtered and washed with several portions of methylene chloride. The organic solution is washed twice with 100 ml. water, 100 ml. brine, dried and evaporated. The tan residue is crystallized from ethanol and from acetonitrile to yield the title compound as white crystals. After addition stirred for 30 minutes filtered directly into a solution of 23.1 g the precipitate is filtered washed with several portions of methylene chloride The organic solution is washed twice with 100 ml brine, dried evaporated The tan residue is crystallized from ethanol and from acetonitrile

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

Procedure: To a cold (-20°) stirred solution of 10.8 g. 1-hydroxymethyl-2-methylcyclopentane prepared by lithium aluminum hydride reduction of methyl 2-methylcyclopentanecarboxylate and 13.4 ml. triethylamine in 300 ml. ether is added dropwise 5.6 ml. methanesulfonyl chloride in 5 ml. of either. After addition is completed, the solution is warmed to room temperature, stirred for 30 minutes and filtered directly into a solution of 23.1 g. ethyl 4-aminophenyl acetate in 100 ml. ether. After 17 hours at room temperature, the precipitate is filtered and washed with several portions of methylene chloride. The organic solution is washed twice with 100 ml. water, 100 ml. brine, dried and evaporated. The tan residue is crystallized from ethanol and from acetonitrile to yield the title compound as white crystals. After addition stirred for 30 minutes filtered directly into a solution of 23.1 g the precipitate is filtered washed with several portions of methylene chloride The organic solution is washed twice with 100 ml brine, dried evaporated The tan residue is crystallized from ethanol and from acetonitrile

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

Procedure: To a solution of (2-methylcyclopent-1-yl)methanol (29 mg, 0.26 mmol) in pentane (0.7 mL) at 0° C. was added 45% HBr in AcOH (0.07 mL, 0.52 mmol). After having been stirred for 30 min, the reaction mixture was washed with brine, saturated aqueous NaHCO3, dried over MgSO4 and filtered with Et2O. This solution was added to a solution of 2-chloro-5-(thiazol-2-ylamino)phenol (59 mg, 0.26 mmol) and Cs2CO3 (85 mg, 0.26 mmol) in acetone (1 mL). After 4 h, the reaction mixture was diluted with AcOEt and washed with 5% aqueous NaOH solution and brine. The organic phase was dried over Na2SO4, concentrated and the crude product was purified by flash chromatography on silica gel (hexane:EtOAc 8/2) to give the product (3 mg, 3% yield). the reaction mixture was washed with brine, saturated aqueous NaHCO3 dried over MgSO4 filtered with Et2O After 4 h washed with 5% aqueous NaOH solution and brine The organic phase was dried over Na2SO4 concentrated the crude product was purified by flash chromatography on silica gel (hexane:EtOAc 8/2)

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

Procedure: To a cold (-20°) stirred solution of 10.8 g. 1-hydroxymethyl-2-methylcyclopentane prepared by lithium aluminum hydride reduction of methyl 2-methylcyclopentanecarboxylate and 13.4 ml. triethylamine in 300 ml. ether is added dropwise 5.6 ml. methanesulfonyl chloride in 5 ml. of either. After addition is completed, the solution is warmed to room temperature, stirred for 30 minutes and filtered directly into a solution of 23.1 g. ethyl 4-aminophenyl acetate in 100 ml. ether. After 17 hours at room temperature, the precipitate is filtered and washed with several portions of methylene chloride. The organic solution is washed twice with 100 ml. water, 100 ml. brine, dried and evaporated. The tan residue is crystallized from ethanol and from acetonitrile to yield the title compound as white crystals. After addition stirred for 30 minutes filtered directly into a solution of 23.1 g the precipitate is filtered washed with several portions of methylene chloride The organic solution is washed twice with 100 ml brine, dried evaporated The tan residue is crystallized from ethanol and from acetonitrile