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

Participants

Reaction Conditions

Reaction Steps

Benzene ruthenium(II)chloride dimmer (0.2 g, 0.0004 mol, 0.02 eq), (1S,2R)-(−)-cis-1-Amino-2-indanol (0.24 g, 0.0016 mol, 0.08 eq) were taken in nitrogen bubbled IPA (50 ml). This solution was heated at 80° C. for 20 min and cooled back to RT. 8-amino-3,4-dihydronaphthalen-2(1H)-one (3.3 g, 0.02 mol) was taken in nitrogen bubbled IPA (98 ml), a solution of KOH (0.23 g, 0.004 mol, 0.2 eq) in IPA (50 ml) and the earlier prepared ruthenium solution were added drop wise simultaneously at RT. The overall reaction mixture was heated to 45° C. and stirred for 30 min at the same temperature. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.2). On completion of the reaction, cooled the reaction contents to rt, filtered on a silica gel bed and the bed was washed with ethyl acetate (4×30 ml). Filtrate was concentrated under reduced pressure, residue was taken in DCM (75 ml) and treated with charcoal. Filtered the contents over a silica gel bed and the bed washed with DCM (4×30 ml). DCM was distilled off completely and the crude obtained was purified by column chromatography (silica gel, 20% ethyl acetate/hexane) to yield the titled product as a brown colored solid (2.1 g, 63% yield, mp 58-87° C.).

Provenance & Evidence