tert-butyl N-[(1S,2R)-2-hydroxycyclohexyl]carbamate

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

Procedure: To a stirred solution of tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 5.34 mmol) in THF (40 mL) was added NaH (60%, 0.32 g, 8.0 mmol) at 0° C. The reaction mixture was stirred at ambient temperature overnight. Saturated aqueous NH4Cl solution was added to quench the reaction. The mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexanes, 2:1) to give (3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-one (0.50 g, 66%) as a white solid. to quench the reaction The mixture was partitioned between EtOAc and water The aqueous layer was extracted with EtOAc The combined organic layers were washed with brine dried concentrated The residue was purified by column chromatography (EtOAc/hexanes, 2:1)

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

Procedure: To a stirred solution of tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 5.34 mmol) in THF (40 mL) was added NaH (60%, 0.32 g, 8.0 mmol) at 0° C. The reaction mixture was stirred at ambient temperature overnight. Saturated aqueous NH4Cl solution was added to quench the reaction. The mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexanes, 2:1) to give (3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-one (0.50 g, 66%) as a white solid. to quench the reaction The mixture was partitioned between EtOAc and water The aqueous layer was extracted with EtOAc The combined organic layers were washed with brine dried concentrated The residue was purified by column chromatography (EtOAc/hexanes, 2:1)

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

Procedure: To a stirred solution of (1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoate (1.95 g, 5.35 mmol) in THF (50 mL) was added a solution of 1N LiOH (9.63 mL, 9.63 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 6 hours and then partitioned between EtOAc and water. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexane, 1:1) to give tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 100%). partitioned between EtOAc and water The organic layer was washed with brine dried concentrated The residue was purified by column chromatography (EtOAc/hexane, 1:1)

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

Procedure: To a stirred solution of tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 5.34 mmol) in THF (40 mL) was added NaH (60%, 0.32 g, 8.0 mmol) at 0° C. The reaction mixture was stirred at ambient temperature overnight. Saturated aqueous NH4Cl solution was added to quench the reaction. The mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexanes, 2:1) to give (3aS,7aR)-hexahydrobenzo[d]oxazol-2(3H)-one (0.50 g, 66%) as a white solid. to quench the reaction The mixture was partitioned between EtOAc and water The aqueous layer was extracted with EtOAc The combined organic layers were washed with brine dried concentrated The residue was purified by column chromatography (EtOAc/hexanes, 2:1)

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

Procedure: To a stirred solution of (1R,2S)-2-(tert-butoxycarbonylamino)cyclohexyl 4-nitrobenzoate (1.95 g, 5.35 mmol) in THF (50 mL) was added a solution of 1N LiOH (9.63 mL, 9.63 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 6 hours and then partitioned between EtOAc and water. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography (EtOAc/hexane, 1:1) to give tert-butyl (1S,2R)-2-hydroxycyclohexylcarbamate (1.15 g, 100%). partitioned between EtOAc and water The organic layer was washed with brine dried concentrated The residue was purified by column chromatography (EtOAc/hexane, 1:1)