tert-butyl 5-oxo-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylate

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

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

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

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

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

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

Procedure: 386 mg of 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.0]-octan-7-one synthesized in accordance with the method described in Tetrahedron, 49, 5047 (1993) was dissolved in 20 ml of ethanol. After adding 65 mg of sodium borohydride, the resulting mixture was stirred at room temperature for 30 minutes. Then the reaction mixture was concentrated under reduced pressure, diluted with ethyl acetate, washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After filtering, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 319 mg of the title compound as white crystals. Then the reaction mixture was concentrated under reduced pressure diluted with ethyl acetate washed with water a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate After filtering the solvent was distilled off under reduced pressure the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

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

Procedure: To a solution of tert-butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (9.57 g, 42.5 mmol) in DCM (170 mL) were added BnNH2 (4.56 g, 42.5 mmol) and AcOH (2.55 g, 42.5 mmol) at 0° C. and the reaction mixture was stirred at 0° C. for 0.5 h. Then NaBH(OAc)3 (18.00 g, 85.0 mmol) was added to the above mixture and the resulting mixture was stirred at rt for another 20 h, then quenched with saturated NaHCO3 solution (142 mL), and extracted with DCM (250 mL×3). The combined organic phases were washed with brine (250 mL×3), dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc) to give the title compound as a yellow solid (7.44 g, 55.3%). the resulting mixture was stirred at rt for another 20 h quenched with saturated NaHCO3 solution (142 mL) extracted with DCM (250 mL×3) The combined organic phases were washed with brine (250 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo The residue was purified by silica gel column chromatography (EtOAc)

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

Procedure: To a solution of tert-butyl 5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (9.57 g, 42.5 mmol) in DCM (170 mL) were added BnNH2 (4.56 g, 42.5 mmol) and AcOH (2.55 g, 42.5 mmol) at 0° C. and the reaction mixture was stirred at 0° C. for 0.5 h. Then NaBH(OAc)3 (18.00 g, 85.0 mmol) was added to the above mixture and the resulting mixture was stirred at rt for another 20 h, then quenched with saturated NaHCO3 solution (142 mL), and extracted with DCM (250 mL×3). The combined organic phases were washed with brine (250 mL×3), dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc) to give the title compound as a yellow solid (7.44 g, 55.3%). the resulting mixture was stirred at rt for another 20 h quenched with saturated NaHCO3 solution (142 mL) extracted with DCM (250 mL×3) The combined organic phases were washed with brine (250 mL×3) dried over anhydrous Na2SO4 concentrated in vacuo The residue was purified by silica gel column chromatography (EtOAc)

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2,2′-(1-(tert-butoxycarbonyl)pyrrolidine-3,4-diyl)diacetic acid (3.40 g, 11.8 mmol) in Ac2O (21 mL) was added NaOAc (0.78 g, 9.5 mmol) and the reaction mixture was stirred at 120° C. for 3 h. After that, the resulting mixture was cooled down to rt then filtered and washed with EtOAc (20 mL×2). The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (EtOAc/PE (v/v)=1/4) to give the title compound as orange yellow oil (1.38 g, 55.0%). After that, the resulting mixture was cooled down to rt then filtered washed with EtOAc (20 mL×2) The filtrate was concentrated in vacuo the residue was purified by silica gel chromatography (EtOAc/PE (v/v)=1/4)

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

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

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