Dimethylformamide → (2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of stage-c product (5 g, 0.026 mol) in DMF (25 ml, 5 times), potassium carbonate (12.64 g, 0.09 mol, 3.5 eq) was added. Cooled the contents to 0° C., phenyl chloroformate (4.5 g (3.63 ml), 0.023 mol) was added drop wise and stirred the contents for 15-20 min. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.5). On completion of the reaction, filtered the contents and washed with ethyl acetate (100 ml). Filtrate was taken in cold water (150 ml), organic layer was separated and dried over sodium sulfate. The solvent removed under reduced pressure and the crude obtained was purified by column chromatography (silica gel, 20% ethyl acetate/hexane) to yield the titled product as a pale yellow colored solid (4.3 g, 53% yield, mp 142-144° C.).

Provenance & Evidence