(1-methylsulfonylpiperidin-4-yl)methanol

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

Procedure: Ethyl 1-(methylsulfonyl)piperidine-4-carboxylate 18 was reacted with lithium aluminum hydride in THF to give 19.

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

Procedure: Ethyl 1-(methylsulfonyl)piperidine-4-carboxylate 18 was reacted with lithium aluminum hydride in THF to give 19.

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

Procedure: A solution of dimethylsulfoxide (39 ml, 0.55 mole) in dichloromethane (300 ml) was added slowly to a solution of oxalyl chloride (22.7 ml, 0.264 mole) in dichloromethane (700 ml) at −60° C. After 10 minutes a solution of 1-methanesulfonylpiperidine-4-methanol (46 grams. 0.238 mole) in dichloromethane (500 ml) was added slowly. After 30 minutes at −60° C., triethylamine (167 ml) was added. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (1.2 liters) and water (200 ml). The organic phase was dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to give 1-methanesulfonylpiperidine-4-carboxaldehyde (34 grams), m.p. 97° C. The mixture was concentrated under reduced pressure the residue was partitioned between ethyl acetate (1.2 liters) and water (200 ml) The organic phase was dried (anhydrous magnesium sulfate) concentrated under reduced pressure The residue was recrystallized from ethyl acetate/hexane

Conditions: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1.0 M lithium aluminum hydride (200 ml, 0.2 mole) in tetrahydrofuran was added dropwise to a solution of 1-methanesulfonylpiperidine-4-carboxylic acid ethyl ester (68 grams, 0.29 mole) in tetrahydrofuran (500 ml) at about +5° C. The reaction mixture was stirred at 5-10° C. for 15 minutes. Water (10 ml) was added dropwise and the mixture was filtered. The filtrate was concentrated under reduced pressure and triturated with 50% ethyl ether-hexane (100 ml). The resulting white solid was collected and dried to give 1-methanesulfonylpiperidine-4-methanol (46 grams, 82%), m.p. 96-97° C. the mixture was filtered The filtrate was concentrated under reduced pressure triturated with 50% ethyl ether-hexane (100 ml) The resulting white solid was collected dried

Conditions: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1.0 M lithium aluminum hydride (200 ml, 0.2 mole) in tetrahydrofuran was added dropwise to a solution of 1-methanesulfonylpiperidine-4-carboxylic acid ethyl ester (68 grams, 0.29 mole) in tetrahydrofuran (500 ml) at about +5° C. The reaction mixture was stirred at 5-10° C. for 15 minutes. Water (10 ml) was added dropwise and the mixture was filtered. The filtrate was concentrated under reduced pressure and triturated with 50% ethyl ether-hexane (100 ml). The resulting white solid was collected and dried to give 1-methanesulfonylpiperidine-4-methanol (46 grams, 82%), m.p. 96-97° C. the mixture was filtered The filtrate was concentrated under reduced pressure triturated with 50% ethyl ether-hexane (100 ml) The resulting white solid was collected dried

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

Procedure: Ethyl 1-(methylsulfonyl)piperidine-4-carboxylate 18 was reacted with lithium aluminum hydride in THF to give 19.

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

Procedure: A solution of dimethylsulfoxide (39 ml, 0.55 mole) in dichloromethane (300 ml) was added slowly to a solution of oxalyl chloride (22.7 ml, 0.264 mole) in dichloromethane (700 ml) at −60° C. After 10 minutes a solution of 1-methanesulfonylpiperidine-4-methanol (46 grams. 0.238 mole) in dichloromethane (500 ml) was added slowly. After 30 minutes at −60° C., triethylamine (167 ml) was added. The mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate (1.2 liters) and water (200 ml). The organic phase was dried (anhydrous magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/hexane to give 1-methanesulfonylpiperidine-4-carboxaldehyde (34 grams), m.p. 97° C. The mixture was concentrated under reduced pressure the residue was partitioned between ethyl acetate (1.2 liters) and water (200 ml) The organic phase was dried (anhydrous magnesium sulfate) concentrated under reduced pressure The residue was recrystallized from ethyl acetate/hexane

Conditions: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 1.0 M lithium aluminum hydride (200 ml, 0.2 mole) in tetrahydrofuran was added dropwise to a solution of 1-methanesulfonylpiperidine-4-carboxylic acid ethyl ester (68 grams, 0.29 mole) in tetrahydrofuran (500 ml) at about +5° C. The reaction mixture was stirred at 5-10° C. for 15 minutes. Water (10 ml) was added dropwise and the mixture was filtered. The filtrate was concentrated under reduced pressure and triturated with 50% ethyl ether-hexane (100 ml). The resulting white solid was collected and dried to give 1-methanesulfonylpiperidine-4-methanol (46 grams, 82%), m.p. 96-97° C. the mixture was filtered The filtrate was concentrated under reduced pressure triturated with 50% ethyl ether-hexane (100 ml) The resulting white solid was collected dried

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

Procedure: Ethyl 1-(methylsulfonyl)piperidine-4-carboxylate 18 was reacted with lithium aluminum hydride in THF to give 19.