Sodium Hydroxide → HCID 59167873, compound

Participants

Reaction Steps

A solution of (R)-2,2,2-trifluoro-N-(7-nitro-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)acetamide (230 mg, 0.6 mmol) and NaOH (108 mg, 2.7 mmol) in a mixed solvent (THF/MeOH/H2O=5 mL/5 mL/1 mL) was heated at 70° C. for 3 h. After cooling to RT, the solvent was evaporated to dryness and the residue was directly loaded on column chomatography (SiO2, EtOAc to EtOAc/2M NH3 in MeOH=100:15 to 100:20) to give (R)-7-nitro-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine (200 mg) as a white solid. Similarly (R)-(1-nitro-5-(2,2,2-trifluoroacetamido)-5,6,7,8-tetrahydronaphthalen-2-yl)methyl acetate was converted to (R)-5-nitro-6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-amine according to the above sequence of reactions.

Provenance & Evidence