methyl 2-(2,3-dihydro-1H-indol-3-yl)acetate

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:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of indoline 75 (8.5 g, 44.2 mmol) in MeOH (150 mL) was added α-D-glucose (27 g, 146 mmol) at room temperature. The mixture was stirred at 70° C. for 60 h, cooled to room temperature and concentrated in vacuo to remove solvent. The residue was purified by silica column chromatography to provide the titled compound 76 (13.7 g, 88%). MH+354. cooled to room temperature concentrated in vacuo to remove solvent The residue was purified by silica column chromatography

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of indole 74 (10.9 g, 57.4 mmol) in trifluoroacetic acid (200 mL) was added triethylsilane (20 mL, 121 mmol) at room temperature. The mixture was stirred at 60° C. for 3 h, cooled to room temperature and concentrated in vacuo to remove solvent. The residue was diluted with EtOAc and washed with aq. saturated Cs2CO3 solution. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 75 (8.5 g, 77%). MH+192. cooled to room temperature concentrated in vacuo to remove solvent The residue was diluted with EtOAc washed with aq. saturated Cs2CO3 solution The organic layer was dried over anhydrous MgSO4 filtered concentrated in vacuo The residue was purified by silica column chromatography

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

Procedure: Methyl (RS)-(2,3-Dihydro-1H-indol-3-yl)acetate (30.0 g, 0.16 mol) was dissolved in tetrahydrofuran (500 mL) and subsequently added to a suspension of lithium aluminium hydride (10.6 g, 0.28 mol) in tetrahydrofuran (500 mL) over a period of 75 min at 33-39° C. The reaction was quenched by sequential addition of water (20 mL), 15% NaOH (10 mL) and water (50 mL), and then MgSO4. The mixture was stirred at room temperature for 1 h, filtered and concentrated in vacuo to give the title compound (24.2 g, 95%). The reaction was quenched by sequential addition of water (20 mL), 15% NaOH (10 mL) and water (50 mL) filtered concentrated in vacuo