Tetrabutylammonium Fluoride → HCID 21919449, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (RS,RS,RS)-(2-tert-butoxycarbonylamino-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-3-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (5.22 g, 10.0 mmol) in tetrabutylammonium fluoride solution (1 M in THF, 42 mL, 42 mmol) was heated 90 min at 50° C. The resultant solution was concentrated in vacuo and chromatographed (CH2Cl2/MeOH/NH4OH 95:5:0.25) to afford the title compound (3.59 g, 95%). Light yellow solid, MS (ISP) 378.4 (M+H)+; tR=7.2 and 18.9 min (Chiralpak® AD 25×0.03 cm, heptane/ethanol/triethylamine 70:30:0.3, flow rate 4 μL/min).

Provenance & Evidence