Tert-Butylamine → n-[6-(Tert-butylamino-methyl)-1,2,3,4-tetrahydro-naphthalen-1-yl]-2-[5,5-dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(r,s)-yl]-acetamide

Participants

Reaction Conditions

Reaction Steps

2-[5,5-Dimethyl-3-oxo-1-(2,4,6-trimethyl-benzenesulfonyl)-piperazin-2(R,S)-yl]-N-(6-formyl-1,2,3,4-tetrahydro-naphthalen-1(R)-yl)-acetamide (Step b, 550 mg, 1.0 mmol) was dissolved in 1,2-dicholoethane (10 mL) and tert-butylamine (1.5 mL). NaBH(OAc)3 (1.5 g, 6.0 mmol) was added to the reaction, and heated to 85° C. in a sealed tube for 18 h. The mixture was cooled to RT, diluted with EtOAc (25 mL), washed with sat. NaHCO3 solution (2×), and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 10% MeOH in CH2Cl2+1% NH3) to provide the title compound. ESMS 583.4 (M+H), 581.5 (M−H).

Provenance & Evidence