2-benzyl-1,3,3a,6,7,7a-hexahydropyrano[3,4-c]pyrrol-4-one

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

Procedure: To a solution of 2-benzylhexahydropyrano[3,4-c]pyrrol-4(2H)-one (2.82 g) in THF (70 mL) was added LiBH4 (0.40 g) at 0° C. under N2. The reaction mixture was stirred for 7 h at room temperature and concentrated in vacuo. The residue was dissolved in MeOH (50 mL) and heated to reflux for 16 h. The mixture was concentrated in vacuo and redissolved in EtOAc (100 mL), then washed with water followed by brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound (2.31 g, 80.62%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 236.3 (M+1). concentrated in vacuo The residue was dissolved in MeOH (50 mL) heated to reflux for 16 h The mixture was concentrated in vacuo redissolved in EtOAc (100 mL) washed with water dried over anhydrous Na2SO4 filtered The filtrate was concentrated in vacuo

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

Procedure: To a solution of 2-benzylhexahydropyrano[3,4-c]pyrrol-4(2H)-one (2.82 g) in THF (70 mL) was added LiBH4 (0.40 g) at 0° C. under N2. The reaction mixture was stirred for 7 h at room temperature and concentrated in vacuo. The residue was dissolved in MeOH (50 mL) and heated to reflux for 16 h. The mixture was concentrated in vacuo and redissolved in EtOAc (100 mL), then washed with water followed by brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound (2.31 g, 80.62%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 236.3 (M+1). concentrated in vacuo The residue was dissolved in MeOH (50 mL) heated to reflux for 16 h The mixture was concentrated in vacuo redissolved in EtOAc (100 mL) washed with water dried over anhydrous Na2SO4 filtered The filtrate was concentrated in vacuo

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

Procedure: To a solution of 5,6-dihydro-2H-pyran-2-one (1.00 g, 1 eq) in CH2Cl2 (150 mL) was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (1.2 eq). After the mixture was cooled to 0° C., a solution of TFA in CH2Cl2 (0.1 eq, 1M) was added slowly. The reaction mixture was slowly heated to room temperature and stirred for 6 h. The reaction mixture was washed with water and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to give the title compound as colorless oil (1.95 g, 82.87%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 232.3 (M+1). The reaction mixture was slowly heated to room temperature The reaction mixture was washed with water and brine dried over anhydrous Na2SO4 concentrated in vacuo The residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA)

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

Procedure: To a solution of 2-benzylhexahydropyrano[3,4-c]pyrrol-4(2H)-one (2.82 g) in THF (70 mL) was added LiBH4 (0.40 g) at 0° C. under N2. The reaction mixture was stirred for 7 h at room temperature and concentrated in vacuo. The residue was dissolved in MeOH (50 mL) and heated to reflux for 16 h. The mixture was concentrated in vacuo and redissolved in EtOAc (100 mL), then washed with water followed by brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound (2.31 g, 80.62%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 236.3 (M+1). concentrated in vacuo The residue was dissolved in MeOH (50 mL) heated to reflux for 16 h The mixture was concentrated in vacuo redissolved in EtOAc (100 mL) washed with water dried over anhydrous Na2SO4 filtered The filtrate was concentrated in vacuo

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

Procedure: To a solution of 5,6-dihydro-2H-pyran-2-one (1.00 g, 1 eq) in CH2Cl2 (150 mL) was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (1.2 eq). After the mixture was cooled to 0° C., a solution of TFA in CH2Cl2 (0.1 eq, 1M) was added slowly. The reaction mixture was slowly heated to room temperature and stirred for 6 h. The reaction mixture was washed with water and brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA) to give the title compound as colorless oil (1.95 g, 82.87%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 232.3 (M+1). The reaction mixture was slowly heated to room temperature The reaction mixture was washed with water and brine dried over anhydrous Na2SO4 concentrated in vacuo The residue was chromatographed with a silica gel column (eluting agent: 2:1 (v/v) PE/EA)