Tyramine → tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

Suspend tyramine (10.0 g, 73.0 mmol) in THF (200 mL). Cool to 0° C. Add a solution of (BOC)2O (31.8 g, 145 mmol) in THF (43 mL). Allow reaction mixture to warm to room temperature overnight. After 20 hours concentrate. Purification through two Waters 500A columns on a Prep LC system 500A to give the title compound: MS FAB ES+ 238.3 (M+H)+, base peak 182.2 (M+2H—C(CH3)3)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm. S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min. 30-99% over 19 min], tR=8.5 min, 100% purity.

Provenance & Evidence