1-(1,3-dihydroisoindol-2-yl)ethanone

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

Procedure: N-Acetylindoline-5-sulphonyl chloride was prepared by a literature method (A. L. Borrer, E. Chinoporos, M. Filosa, S. R. Herrchen, C. R. Petersen, C. A. Stern, J. Org. Chem. 53, 2047 (1988)) as was N-acetylindoline-6-sulphonyl chloride (P. R. Carlier, M. P. Lockshin, M. P. Filosa, J. Org. Chem. 59, 3232 (1994)). N-Acetylisoindoline-5-sulphonyl chloride was prepared from N-acetylisoindoline and chlorosulphonic acid in analogy to N-acetylindoline-5-sulphonyl chloride.

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

Procedure: N-Acetylindoline-5-sulphonyl chloride was prepared by a literature method (A. L. Borrer, E. Chinoporos, M. Filosa, S. R. Herrchen, C. R. Petersen, C. A. Stern, J. Org. Chem. 53, 2047 (1988)) as was N-acetylindoline-6-sulphonyl chloride (P. R. Carlier, M. P. Lockshin, M. P. Filosa, J. Org. Chem. 59, 3232 (1994)). N-Acetylisoindoline-5-sulphonyl chloride was prepared from N-acetylisoindoline and chlorosulphonic acid in analogy to N-acetylindoline-5-sulphonyl chloride.

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

Procedure: N-Acetylindoline-5-sulphonyl chloride was prepared by a literature method (A. L. Borrer, E. Chinoporos, M. Filosa, S. R. Herrchen, C. R. Petersen, C. A. Stern, J. Org. Chem. 53, 2047 (1988)) as was N-acetylindoline-6-sulphonyl chloride (P. R. Carlier, M. P. Lockshin, M. P. Filosa, J. Org. Chem. 59, 3232 (1994)). N-Acetylisoindoline-5-sulphonyl chloride was prepared from N-acetylisoindoline and chlorosulphonic acid in analogy to N-acetylindoline-5-sulphonyl chloride.

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

Procedure: In a 3-liter GL autoclave fitted with a electromagnetic stirrer are added 175 g of N-acetylisoindoline, 825 g of methylalcohol and 17 g of 5% ruthenium-carbon catalyst (50% water-containing). The reaction mixture is subjected to a hydrogen-pressure of 20 kg/cm2 and a temperature of 110° C. After a 8 hour hydrogen introduction, the drop in the rate of the hydrogen-absorption is observed, at this point the introduction of hydrogen is ceased to terminate the reaction. After the termination of reaction, the catalyst is filtered out from the reacted solution. By the result of the capillary chromatographic analysis, the yield of cis-hexahydro-N-acetylisoindoline is 93.7%. In addition, 0.2% of trans-hexahydro-N-acetylisoindoline is formed. In a 3-liter GL autoclave fitted with a electromagnetic stirrer a temperature of 110° C the drop in the rate of the hydrogen-absorption to terminate the reaction After the termination of reaction the catalyst is filtered out from the reacted solution By the result of the capillary chromatographic analysis