methyl 3-[[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]benzoate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Lithium hydroxide monohydrate (420 mg, 10 mmol) and water (15 ml) were added to a solution of tert-butyl N-methyl-N-(3-(methyloxycarbonyl)benzyl)carbamate (1.6 g, 5.6 mmol) in dioxan (20 ml) and the mixture was stirred for 2 h. The dioxan was removed in vacuo and the residue was taken up in 0.3N potassium hydrogen sulphate. The mixture was extracted with ethyl acetate and the organic phase was washed with water and brine, dried and reduced to afford tert-butyl N-(3-carboxybenzyl)-N-methylcarbamate (1.4 g, 95%). The dioxan was removed in vacuo The mixture was extracted with ethyl acetate the organic phase was washed with water and brine dried

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Dissolve 3-[(tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acid methyl ester (1.70 g, 6.1 mmol) in tetrahydrofuran (60 mL) at 0° C. Add a 1M solution of lithium aluminum hydride in tetrahydrofuran (8 mL, 8 mmol) dropwise and stir for 2 hrs. Quench the reaction with water (3 mL), 5N sodium hydroxide solution (3 mL) and more water (9 mL), filter and concentrate. Purify the residue by chromatography (silica gel) eluting with 40-60% ethyl acetate/hexanes to provide the title compound (1.42 g, 93%). Quench the reaction with water (3 mL), 5N sodium hydroxide solution (3 mL) and more water (9 mL) filter concentrate Purify the residue by chromatography (silica gel) eluting with 40-60% ethyl acetate/hexanes

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

Procedure: Dissolve 3-[(tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acid methyl ester (1.70 g, 6.1 mmol) in tetrahydrofuran (60 mL) at 0° C. Add a 1M solution of lithium aluminum hydride in tetrahydrofuran (8 mL, 8 mmol) dropwise and stir for 2 hrs. Quench the reaction with water (3 mL), 5N sodium hydroxide solution (3 mL) and more water (9 mL), filter and concentrate. Purify the residue by chromatography (silica gel) eluting with 40-60% ethyl acetate/hexanes to provide the title compound (1.42 g, 93%). Quench the reaction with water (3 mL), 5N sodium hydroxide solution (3 mL) and more water (9 mL) filter concentrate Purify the residue by chromatography (silica gel) eluting with 40-60% ethyl acetate/hexanes

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

Procedure: Dissolve 3-(tert-butoxycarbonylamino-methyl)-benzoic acid methyl ester (2.80 g, 10.6 mmol) in dimethylformamide (60 mL). Add 60% sodium hydride dispersion in oil (0.52 g, 13 mmol). Stir for 1 hr. Add methyl iodide (0.81 mL, 13 mmol) and stir for additional 1 hr. Quench the reaction with water and concentrate. Partition the residue between ethyl acetate and water. Separate the organic layer and dry over sodium sulfate. Filter and concentrate. Purify the residue by chromatography (silica gel) eluting with 15-25% ethyl acetate/hexane to provide the title compound (1.70 g, 57%). Quench the reaction with water concentrate Partition the residue between ethyl acetate and water Separate the organic layer dry over sodium sulfate Filter concentrate Purify the residue by chromatography (silica gel) eluting with 15-25% ethyl acetate/hexane

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

Procedure: Lithium hydroxide monohydrate (420 mg, 10 mmol) and water (15 ml) were added to a solution of tert-butyl N-methyl-N-(3-(methyloxycarbonyl)benzyl)carbamate (1.6 g, 5.6 mmol) in dioxan (20 ml) and the mixture was stirred for 2 h. The dioxan was removed in vacuo and the residue was taken up in 0.3N potassium hydrogen sulphate. The mixture was extracted with ethyl acetate and the organic phase was washed with water and brine, dried and reduced to afford tert-butyl N-(3-carboxybenzyl)-N-methylcarbamate (1.4 g, 95%). The dioxan was removed in vacuo The mixture was extracted with ethyl acetate the organic phase was washed with water and brine dried