[(2S)-5,5-dimethyloxolan-2-yl]methanol

Conditions: temp:8.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of (S)-(5,5-dimethyltetrahydrofuran-2-yl)methanol (14 g, 108 mmol) and PPh3 (33.8 g, 129 mmol) in THF (140 ml) under N2 was added phthalimide (17.40 g, 118 mmol) to give a suspension. The mixture was cooled to 8° C. and DIAD (27.2 ml, 140 mmol) was added dropwise over 30 mins keeping internal T<10° C. The resulting white slurry was diluted with water (100 ml) and extracted with EtOAc (100 ml). The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) and dried (MgSO4) and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane afforded the title compound as a white crystalline solid; to give a suspension T<10° C extracted with EtOAc (100 ml) The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) dried (MgSO4) concentrated under reduced pressure Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane

Conditions: temp:8.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of (S)-(5,5-dimethyltetrahydrofuran-2-yl)methanol (14 g, 108 mmol) and PPh3 (33.8 g, 129 mmol) in THF (140 ml) under N2 was added phthalimide (17.40 g, 118 mmol) to give a suspension. The mixture was cooled to 8° C. and DIAD (27.2 ml, 140 mmol) was added dropwise over 30 mins keeping internal T<10° C. The resulting white slurry was diluted with water (100 ml) and extracted with EtOAc (100 ml). The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) and dried (MgSO4) and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane afforded the title compound as a white crystalline solid; to give a suspension T<10° C extracted with EtOAc (100 ml) The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) dried (MgSO4) concentrated under reduced pressure Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane

Conditions: temp:8.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of (S)-(5,5-dimethyltetrahydrofuran-2-yl)methanol (14 g, 108 mmol) and PPh3 (33.8 g, 129 mmol) in THF (140 ml) under N2 was added phthalimide (17.40 g, 118 mmol) to give a suspension. The mixture was cooled to 8° C. and DIAD (27.2 ml, 140 mmol) was added dropwise over 30 mins keeping internal T<10° C. The resulting white slurry was diluted with water (100 ml) and extracted with EtOAc (100 ml). The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) and dried (MgSO4) and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane afforded the title compound as a white crystalline solid; to give a suspension T<10° C extracted with EtOAc (100 ml) The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) dried (MgSO4) concentrated under reduced pressure Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane

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

Procedure: To a stirred solution of compound A92-2 (1.03 g, 4.43 mmol) in MeOH (8 mL) was added p-toluenesulfonic acid monohydrate (421 mg, 2.2 mmol) at room temperature and the mixture was refluxed for 5 h. The reaction mixture was cooled to room temperature, quenched with water (15 mL) and extracted with DCM (2×25 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 35% EtOAc/hexane as eluent) to provide compound A92-3 (330 mg, 57%) as a colorless gum. the mixture was refluxed for 5 h quenched with water (15 mL) extracted with DCM (2×25 mL) The combined organic layers were washed with brine (20 mL) dried over anhydrous Na2SO4 concentrated under reduced pressure The residue was purified by column chromatography (silica gel, 35% EtOAc/hexane as eluent) to provide compound A92-3 (330 mg, 57%) as a colorless gum

Conditions: temp:8.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of (S)-(5,5-dimethyltetrahydrofuran-2-yl)methanol (14 g, 108 mmol) and PPh3 (33.8 g, 129 mmol) in THF (140 ml) under N2 was added phthalimide (17.40 g, 118 mmol) to give a suspension. The mixture was cooled to 8° C. and DIAD (27.2 ml, 140 mmol) was added dropwise over 30 mins keeping internal T<10° C. The resulting white slurry was diluted with water (100 ml) and extracted with EtOAc (100 ml). The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) and dried (MgSO4) and concentrated under reduced pressure. Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane afforded the title compound as a white crystalline solid; to give a suspension T<10° C extracted with EtOAc (100 ml) The organics were washed with sat. NaHCO3 (100 ml), brine (100 ml) dried (MgSO4) concentrated under reduced pressure Purification by chromatography on silica eluting with 0-20% EtOAc/iso-hexane