tert-butyl N-[(1S)-2-(3,5-difluorophenyl)-1-[(2R)-oxiran-2-yl]ethyl]carbamate

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

Procedure: Vinylmagnesium bromide was added to copper (I) bromide-dimethyl sulfide complex in tetrahydrofuran at low temperature. Tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2R)-oxiran-2-yl]ethylcarbamate (31) in tetrahydrofuran was added. At room temperature, the reaction was quenched with saturated ammonium chloride, extracted, and dried over sodium sulfate. A white solid (32) was obtained upon concentration. At room temperature, the reaction was quenched with saturated ammonium chloride extracted dried over sodium sulfate

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

Procedure: Mesylate 30 was dissolved in methanol/water at 0° and a solution of sodium hydroxide in water was added. After all of the starting material was consumed, the reaction was extracted and the residue purified using silica gel chromatography to obtain epoxide 31 as a white solid, m.p.=99°. After all of the starting material was consumed the reaction was extracted the residue purified

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

Procedure: Vinylmagnesium bromide was added to copper (I) bromide-dimethyl sulfide complex in tetrahydrofuran at low temperature. Tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2R)-oxiran-2-yl]ethylcarbamate (31) in tetrahydrofuran was added. At room temperature, the reaction was quenched with saturated ammonium chloride, extracted, and dried over sodium sulfate. A white solid (32) was obtained upon concentration. At room temperature, the reaction was quenched with saturated ammonium chloride extracted dried over sodium sulfate

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

Procedure: Mesylate 30 was dissolved in methanol/water at 0° and a solution of sodium hydroxide in water was added. After all of the starting material was consumed, the reaction was extracted and the residue purified using silica gel chromatography to obtain epoxide 31 as a white solid, m.p.=99°. After all of the starting material was consumed the reaction was extracted the residue purified

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (1S,2S)-[2-(3,5-Difluorophenyl)-1-oxiranylethyl]-carbamic acid tert-butyl ester (VI, 113 mg) and 1-((3aS,8aR)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-butan-1-one (VII, 94 mg) were combined in dry THF (3 mL), and cooled to −78° C. To this solution was added BuLi (2.5 M in hexanes, 0.32 mL) over 5 min., whereupon the solution was allowed to warm to 0° C. for 1.5 h. The reaction mixture was partitioned between 0.5 N HCl (4 mL) and 1:1 EtOAc/hexanes (2×4 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (20-30% EtOAc/hexanes) to give an oil: MH+559.1. to warm to 0° C. for 1.5 h The reaction mixture was partitioned between 0.5 N HCl (4 mL) and 1:1 EtOAc/hexanes (2×4 mL) The combined organic layers were dried (MgSO4) filtered concentrated under reduced pressure The residue was purified by flash chromatography (20-30% EtOAc/hexanes) to give an oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (1S, 2S)-[2-(3,5-Difluorophenyl)-1-oxiranylethyl]-carbamic acid tert-butyl ester (VI, 113 mg) and 1-((3aS, 8aR)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-butan-1-one (VII, 94 mg) were combined in dry THF (3 mL), and cooled to −78° C. To this solution was added BuLi (2.5 M in hexanes, 0.32 mL) over 5 min., whereupon the solution was allowed to warm to 0° C. for 1.5 h. The reaction mixture was partitioned between 0.5 N HCl (4 mL) and 1:1 EtOAc/hexanes (2×4 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (20-30% EtOAc/hexanes) to give an oil: MH+559.1. to warm to 0° C. for 1.5 h The reaction mixture was partitioned between 0.5 N HCl (4 mL) and 1:1 EtOAc/hexanes (2×4 mL) The combined organic layers were dried (MgSO4) filtered concentrated under reduced pressure The residue was purified by flash chromatography (20-30% EtOAc/hexanes) to give an oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (1S,2S)-[2-(3,5-Difluorophenyl)-1-oxiranylethyl]-carbamic acid tert-butyl ester (VI, 113 mg) and 1-((3aS,8aR)-2,2-Dimethyl-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-3-yl)-butan-1-one (VII, 94 mg) were combined in dry THF (3 mL), and cooled to −78° C. To this solution was added BuLi (2.5 M in hexanes, 0.32 mL) over 5 min., whereupon the solution was allowed to warm to 0° C. for 1.5 h. The reaction mixture was partitioned between 0.5 N HCl (4 mL) and 1:1 EtOAc/hexanes (2×4 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (20–30% EtOAc/hexanes) to give an oil: MH+559.1. to warm to 0° C. for 1.5 h The reaction mixture was partitioned between 0.5 N HCl (4 mL) and 1:1 EtOAc/hexanes (2×4 mL) The combined organic layers were dried (MgSO4) filtered concentrated under reduced pressure The residue was purified by flash chromatography (20–30% EtOAc/hexanes) to give an oil

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

Procedure: Vinylmagnesium bromide was added to copper (I) bromide-dimethyl sulfide complex in tetrahydrofuran at low temperature. Tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2R)-oxiran-2-yl]ethylcarbamate (31) in tetrahydrofuran was added. At room temperature, the reaction was quenched with saturated ammonium chloride, extracted, and dried over sodium sulfate. A white solid (32) was obtained upon concentration. At room temperature, the reaction was quenched with saturated ammonium chloride extracted dried over sodium sulfate

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

Procedure: Mesylate 30 was dissolved in methanol/water at 0° and a solution of sodium hydroxide in water was added. After all of the starting material was consumed, the reaction was extracted and the residue purified using silica gel chromatography to obtain epoxide 31 as a white solid, m.p.=99°. After all of the starting material was consumed the reaction was extracted the residue purified