(1-propylcyclobutyl)methanol

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

Procedure: An ice-cold mixture of 4-methylmorpholine N-oxide (NMO) (1.683 g, 14.4 mmol), 1-3 (1.229 g, 9.59 mmol) and 4 Å molecular sieves (5.5 g) in dichloromethane (20 mL) was treated with tetrapropylammonium perruthenate (TPAP) (179 mg, 0.51 mmol). The mixture was stirred at 0° C. for 5 min. and then was allowed to warm to room temperature. After 1 h, the mixture was filtered through a pad of silica gel (dichloromethane) and the dichloromethane was evaporated. The crude product was combined with the crude product from another batch (starting with 4.986 g, 38.9 mmol of 1-3) and the combined product was purified by distillation under reduced pressure followed by flash chromatography on silica gel (15% ether/pentane) to give 1-4 (2.649 g, 43%). to warm to room temperature After 1 h the mixture was filtered through a pad of silica gel (dichloromethane) the dichloromethane was evaporated the combined product was purified by distillation under reduced pressure

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

Procedure: LiBH4 (524 mg, 24 mmol) and methanol (1 mL) were added to a 0° C. solution of 1-2 (1.935 g, 11.4 mmol) in ether (22 mL). After 1 h at 0° C. and 1.5 h at room temperature, 41 mL 2 M NaOH was slowly added and the resulting mixture was stirred for 1 h. The mixture was then extracted with dichloromethane (3×40 mL) and the combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each). The organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (dichloromethane) gave 1-3 (1.229 g, 87%). The mixture was then extracted with dichloromethane (3×40 mL) the combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each) The organic solution was then dried (Na2SO4) filtered evaporated Purification by flash chromatography on silica gel (dichloromethane)

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

Procedure: An ice-cold mixture of 4-methylmorpholine N-oxide (NMO) (1.683 g, 14.4 mmol), 1-3 (1.229 g, 9.59 mmol) and 4 Å molecular sieves (5.5 g) in dichloromethane (20 mL) was treated with tetrapropylammonium perruthenate (TPAP) (179 mg, 0.51 mmol). The mixture was stirred at 0° C. for 5 min. and then was allowed to warm to room temperature. After 1 h, the mixture was filtered through a pad of silica gel (dichloromethane) and the dichloromethane was evaporated. The crude product was combined with the crude product from another batch (starting with 4.986 g, 38.9 mmol of 1-3) and the combined product was purified by distillation under reduced pressure followed by flash chromatography on silica gel (15% ether/pentane) to give 1-4 (2.649 g, 43%). to warm to room temperature After 1 h the mixture was filtered through a pad of silica gel (dichloromethane) the dichloromethane was evaporated the combined product was purified by distillation under reduced pressure

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

Procedure: LiBH4 (524 mg, 24 mmol) and methanol (1 mL) were added to a 0° C. solution of 1-2 (1.935 g, 11.4 mmol) in ether (22 mL). After 1 h at 0° C. and 1.5 h at room temperature, 41 mL 2 M NaOH was slowly added and the resulting mixture was stirred for 1 h. The mixture was then extracted with dichloromethane (3×40 mL) and the combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each). The organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (dichloromethane) gave 1-3 (1.229 g, 87%). The mixture was then extracted with dichloromethane (3×40 mL) the combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each) The organic solution was then dried (Na2SO4) filtered evaporated Purification by flash chromatography on silica gel (dichloromethane)

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

Procedure: An ice-cold mixture of 4-methylmorpholine N-oxide (NMO) (1.683 g, 14.4 mmol), 1-3 (1.229 g, 9.59 mmol) and 4 Å molecular sieves (5.5 g) in dichloromethane (20 mL) was treated with tetrapropylammonium perruthenate (TPAP) (179 mg, 0.51 mmol). The mixture was stirred at 0° C. for 5 min. and then was allowed to warm to room temperature. After 1 h, the mixture was filtered through a pad of silica gel (dichloromethane) and the dichloromethane was evaporated. The crude product was combined with the crude product from another batch (starting with 4.986 g, 38.9 mmol of 1-3) and the combined product was purified by distillation under reduced pressure followed by flash chromatography on silica gel (15% ether/pentane) to give 1-4 (2.649 g, 43%). to warm to room temperature After 1 h the mixture was filtered through a pad of silica gel (dichloromethane) the dichloromethane was evaporated the combined product was purified by distillation under reduced pressure

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

Procedure: LiBH4 (524 mg, 24 mmol) and methanol (1 mL) were added to a 0° C. solution of 1-2 (1.935 g, 11.4 mmol) in ether (22 mL). After 1 h at 0° C. and 1.5 h at room temperature, 41 mL 2 M NaOH was slowly added and the resulting mixture was stirred for 1 h. The mixture was then extracted with dichloromethane (3×40 mL) and the combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each). The organic solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (dichloromethane) gave 1-3 (1.229 g, 87%). The mixture was then extracted with dichloromethane (3×40 mL) the combined dichloromethane solution was washed with saturated NH4Cl solution and brine (150 mL each) The organic solution was then dried (Na2SO4) filtered evaporated Purification by flash chromatography on silica gel (dichloromethane)