Cyclopenta[c]pyrrole-2(1H)-carboxylic acid, hexahydro-5-hydroxy-, 1,1-diMethylethyl ester

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:0.00; 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: To a solution of the title compound from Step A above (550 mg, 2.4 mmol) and DMAP (296 mg) in DCM (15 mL) was added MsCl (189 μL) at 0° C. The mixture was stirred for 10 min at the same temperature and for an additional hour at RT. The mixture was quenched with ice water and extracted with ethyl acetate (2×50 mL). The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue oil was purified via prep-plate purification eluting with 50% ethyl acetate in hexane to afford the title compound (i-39) (555 mg, 75%). ESI-MS calculated for C13H23NO5S: Exact Mass: 305.13. Found 328.14 (MNa)+. The mixture was quenched with ice water extracted with ethyl acetate (2×50 mL) The organic layer was washed with water and brine dried over sodium sulfate filtered concentrated under vacuum The residue oil was purified via prep-plate purification eluting with 50% ethyl acetate in hexane

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)