(1R,2R)-2-phenylcyclopropane-1-carbaldehyde

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

Procedure: A solution of 1H-pyrazole-4-carboxylic acid (piperidin-4-ylmethyl)-amide (290 mg, 1.39 mmol), trans-2-phenylcyclopropanecarbaldehyde (224 mg, 1.53 mmol) and sodium triacetoxyborohydride (590 mg, 2.78 mmol) in MeOH (15 mL) was heated to 50° C. and stirred for 1 h. The resulting reaction mixture was concentrated and purified by silica gel chromatography (gradient: CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH) to give the trans 1H-pyrazole-4-carboxylic acid [1-(2-phenyl-cyclopropylmethyl)-piperidin-4-ylmethyl]-amide product. The resulting reaction mixture was concentrated purified by silica gel chromatography (gradient: CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH)

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

Procedure: A solution of 1H-pyrazole-4-carboxylic acid (piperidin-4-ylmethyl)-amide (290 mg, 1.39 mmol), trans-2-phenylcyclopropanecarbaldehyde (224 mg, 1.53 mmol) and sodium triacetoxyborohydride (590 mg, 2.78 mmol) in MeOH (15 mL) was heated to 50° C. and stirred for 1 h. The resulting reaction mixture was concentrated and purified by silica gel chromatography (gradient: CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH) to give the trans 1H-pyrazole-4-carboxylic acid [1-(2-phenyl-cyclopropylmethyl)-piperidin-4-ylmethyl]-amide product. The resulting reaction mixture was concentrated purified by silica gel chromatography (gradient: CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH)

Conditions: temp:22.01; pressure:0.00; stir:

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

Procedure: A solution of trans-2-phenylcyclopropanecarbaldehyde rac-I-6B (0.89 g, 6.1 mmol) in EtOH (12 mL) and cooled to 0°C. was treated with hydroxylamine hydrochloride (0.43 g, 6.1 mmol) and Na2CO3. The reaction mixture was allowed to warm to rt and stir fo(12 h. The volatiles were removed in vacuo and extracted with EtOAc. The organics were collected, dried over Na2SO4 filtered, and concentrated to afford trans-2-Phenylcyclopropanecarbaldehyde oxime which was used without further purification. 12 h The volatiles were removed in vacuo extracted with EtOAc The organics were collected dried over Na2SO4 filtered concentrated

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

Procedure: 104 mg of the alcohol was dissolved in 5 ml of chloroform and stirred with 445 mg of the Dess-Martin reagent (periodinane) at room temperature for 30 minutes. The reaction solution was poured into a mixture of saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1] to give 52 mg of the title compound as a colorless oily substance. extracted with ethyl acetate The organic layer was dried over anhydrous magnesium sulfate The desiccant was filtered off the solvent was distilled off under reduced pressure The residue was purified by silica gel column chromatography [hexane/ethyl acetate=10/1]

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

Procedure: A solution of 1H-pyrazole-4-carboxylic acid (piperidin-4-ylmethyl)-amide (290 mg, 1.39 mmol), trans-2-phenylcyclopropanecarbaldehyde (224 mg, 1.53 mmol) and sodium triacetoxyborohydride (590 mg, 2.78 mmol) in MeOH (15 mL) was heated to 50° C. and stirred for 1 h. The resulting reaction mixture was concentrated and purified by silica gel chromatography (gradient: CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH) to give the trans 1H-pyrazole-4-carboxylic acid [1-(2-phenyl-cyclopropylmethyl)-piperidin-4-ylmethyl]-amide product. The resulting reaction mixture was concentrated purified by silica gel chromatography (gradient: CH2Cl2 to 80:20:2 CH2Cl2:MeOH:NH4OH)