2-(2-bromo-3-methylanilino)ethanol

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

Procedure: To a solution of THF were added successively potassium tert-butoxide (572 mg, 5.10 mmol), 2-(2-bromo-3-methylphenylamino)ethanol (1151 mg, 5 mmol) and ethyl 2-chloroacetate (0.565 mL, 5.30 mmol). The resulting suspension was stirred for 16 h at RT. Additional KOtBu (200 mg) and ethyl 2-chloroacetate (0.15 ml) were added and the reaction mixture was heated to 36° C. for additional 2 h. The reaction was quenched with water and 1M HCl, followed by addition of EtOAc. The organic phase was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (5-70% EtOAc/hexanes). 4-(2-Bromo-3-methylphenyl)morpholin-3-one was obtained as a light-yellow powder. the reaction mixture was heated to 36° C. for additional 2 h The reaction was quenched with water and 1M HCl followed by addition of EtOAc The organic phase was separated washed with brine dried over MgSO4 The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (5-70% EtOAc/hexanes)

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

Procedure: To a 50-mL RBF was added 2-bromo-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylaniline (1.43 g, 4.15 mmol) and THF (10 mL). A solution of TBAF (1.0M in THF; 4.98 mL, 4.98 mmol) was added dropwise at RT. The reaction mixture was allowed to stir for 1.5 h at RT. The solvent was removed under reduced pressure. The remaining residue was purified by flash chromatography (5-60% EtOAc/hexanes). 2-(2-Bromo-3-methylphenylamino)ethanol was isolated as a clear yellow oil. The solvent was removed under reduced pressure The remaining residue was purified by flash chromatography (5-60% EtOAc/hexanes)

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

Procedure: To a 50-mL RBF was added 2-bromo-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylaniline (1.43 g, 4.15 mmol) and THF (10 mL). A solution of TBAF (1.0M in THF; 4.98 mL, 4.98 mmol) was added dropwise at RT. The reaction mixture was allowed to stir for 1.5 h at RT. The solvent was removed under reduced pressure. The remaining residue was purified by flash chromatography (5-60% EtOAc/hexanes). 2-(2-Bromo-3-methylphenylamino)ethanol was isolated as a clear yellow oil. The solvent was removed under reduced pressure The remaining residue was purified by flash chromatography (5-60% EtOAc/hexanes)

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

Procedure: To a solution of THF were added successively potassium tert-butoxide (572 mg, 5.10 mmol), 2-(2-bromo-3-methylphenylamino)ethanol (1151 mg, 5 mmol) and ethyl 2-chloroacetate (0.565 mL, 5.30 mmol). The resulting suspension was stirred for 16 h at RT. Additional KOtBu (200 mg) and ethyl 2-chloroacetate (0.15 ml) were added and the reaction mixture was heated to 36° C. for additional 2 h. The reaction was quenched with water and 1M HCl, followed by addition of EtOAc. The organic phase was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (5-70% EtOAc/hexanes). 4-(2-Bromo-3-methylphenyl)morpholin-3-one was obtained as a light-yellow powder. the reaction mixture was heated to 36° C. for additional 2 h The reaction was quenched with water and 1M HCl followed by addition of EtOAc The organic phase was separated washed with brine dried over MgSO4 The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (5-70% EtOAc/hexanes)

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

Procedure: To a 50-mL RBF was added 2-bromo-N-(2-(tert-butyldimethylsilyloxy)ethyl)-3-methylaniline (1.43 g, 4.15 mmol) and THF (10 mL). A solution of TBAF (1.0M in THF; 4.98 mL, 4.98 mmol) was added dropwise at RT. The reaction mixture was allowed to stir for 1.5 h at RT. The solvent was removed under reduced pressure. The remaining residue was purified by flash chromatography (5-60% EtOAc/hexanes). 2-(2-Bromo-3-methylphenylamino)ethanol was isolated as a clear yellow oil. The solvent was removed under reduced pressure The remaining residue was purified by flash chromatography (5-60% EtOAc/hexanes)