Tetrabutylammonium Fluoride → HCID 58109397, compound

Participants

Reaction Steps

To a solution of (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-((S)-1-(4-(methoxymethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (7 mg, 0.02 mmol) in EtOAc (5 mL) was added TBAF (26.1 mg, 0.10 mmol) at rt, and the mixture was stirred at rt overnight. The mixture was concentrated in vacuo to give the crude product, which was purified by preparative TLC followed by preparative HPLC to afford (R)-6-(3-hydroxypropyl)-3-((S)-1-(4-(methoxymethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (1.63 mg). LC-MS Method 3 tR=0.96, min, m/z=406; 1H NMR (CDCl3): 1.39 (m, 1H), 1.49 (m, 3H), 1.71 (m, 1H), 1.89 (m, 3H), 2.01 (m, 1H), 2.18 (m, 2H), 2.75-2.88 (m, 3H), 3.23 (m, 1H), 3.48 (m, 1H), 3.70 (m, 1H) □4.19 (m, 1H), 5.58 (m, 1H), 6.73-6.86 (m, 2H), 7.08-7.29 (m, 6H).

Provenance & Evidence