2,3-dihydro-1H-indol-2-ylmethanol

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 solution of 5.12 g of ethyl indoline-2-carboxylate (prepared as described in Preparation 1) in 20 ml of anhydrous tetrahydrofuran was added dropwise, whilst ice-cooling, to a mixture of 1.20 g of lithium aluminum hydride and 80 ml of anhydrous tetrahydrcfuran, and the resulting mixture was stirred at room temperature for 2 hours. After this, an excess of sodium sulfate decahydrate was added to the mixture, which was then stirred for 20 minutes. At the end of this time, insoluble materials were filtered off and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 3.81 g of the title compound having Rf=0.16 (on silica gel thin layer chromatography using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent). was then stirred for 20 minutes At the end of this time, insoluble materials were filtered off the filtrate was concentrated by evaporation under reduced pressure The concentrate was purified by column chromatography through silica gel by volume mixture of hexane and ethyl acetate as the eluent

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

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (RS)-2-Hydroxymethylindoline (29.8 g) is dissolved in a mixture of 34 N sulphuric acid (11.5 cc) and water (60 cc). The mixture is heated whilst distilling the water under reduced pressure (10 mm Hg), the heating bath being raised gradually to 160° C., which temperature is maintained for 2 hours. (RS)-2-Hydroxysulphonyloxymethylindoline (45.8 g) is thus obtained in the form of white crystals. The mixture is heated whilst distilling the water under reduced pressure (10 mm Hg) which temperature is maintained for 2 hours