tert-butyl 3-(methylsulfonyloxymethyl)azetidine-1-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:

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: A mixture of 1-Boc-3-methylsulfonyloxymethyl-azetidine (1.47 g), 3-nitro-5-trifluoromethyl-phenol (1.15 g) and K2CO3 (1.15 g) in DMF (20 ml) at 80° C. was stirred overnight. The reaction was cooled to RT and diluted with 25 mL of sat. NaHCO3 and 50 mL of EtOAc. The organic phase was separated and washed with brine (25 mL), dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography (50% EtOAc/hex). The organic phase was separated washed with brine (25 mL) dried over Na2SO4 concentrated in vacuo The crude compound was purified by column chromatography (50% EtOAc/hex)

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

Procedure: A mixture of 1-Boc-3-methylsulfonyloxymethyl-azetidine (1.47 g), 3-nitro-5-trifluoromethyl-phenol (1.15 g) and K2CO3 (1.15 g) in DMF(20 ml) at 80° C. was stirred overnight. The reaction was cooled to RT and diluted with 25 mL of sat. NaHCO3 and 50 mL of EtOAc. The organic phase was separated and washed with brine (25 mL), dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography (50% EtOAc/hex). The organic phase was separated washed with brine (25 mL) dried over Na2SO4 concentrated in vacuo The crude compound was purified by column chromatography (50% EtOAc/hex)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the mixture of 2-chloro-5-nitro-phenol (1.31 g, 7.54 mmol) and K2CO3 (1.57 g, 11.31 mmol) in 20 mL of DMF was added 3-methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester (2.0 g, 7.54 mol). The reaction mixture was stirred at 50° C. for 1 h. After cooling to RT, the reaction mixture was diluted in 100 mL of EtOAc and quenched with 50 mL of water. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×50 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuum. The title compound was obtained via column chromatography (silica gel, 1;1 hexane/EtOAc) as yellow oil with 93% yield. After cooling to RT quenched with 50 mL of water The organic layer was separated the aqueous layer was extracted with EtOAc (2×50 mL) The combined organic phases were washed with brine dried over MgSO4 concentrated in vacuum