Water → HCID 58109499, compound

Participants

Reaction Steps

A stirred solution of BH3.Me2S (0.7 mL, 7.0 mmol) in dry THF (7 mL) was cooled in an ice bath and 2 M 2-methylbutene in THF (7 mL, 14 mmol) was added dropwise over 3 min. The mixture was stirred in the ice bath for 1.5 h. An aliquot of this solution (0.25 mL, 0.12 mmol) was added to an ice-cold solution of 6-allyl-3-(2,4-dichlorobenzyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (3.2 mg, 8.0 μmol) in dry THF (0.5 mL). The mixture was stirred overnight at rt. Water (2 mL) was added and the mixture was stirred for 3 h. Solid NaBO3.H2O (10 mg) was added. The mixture was stirred overnight, applied to a 10-mL ChemElut cartridge and eluted with CH2Cl2 (20 mL). The eluate was concentrated and the residue was purified by prep HPLC to afford 3-(2,4-dichlorobenzyl)-6-(4-fluorophenyl)-6-(3-hydroxypropyl)-1,3-oxazinan-2-one (1.3 mg, 39%). LC-MS Method 1 tR=1.78 min, m/z=368; 1H NMR (CDCl3) 1.37 (m, 1H), 1.66 (m, 1H), 1.99 (m, 2H), 2.30 (m, 2H), 2.92 (m, 1H), 3.10 (m, 1H), 3.58 (t, 2H), 4.50 (d, 1H), 4.63 (d, 1H), 6.90-7.35 (7H).

Provenance & Evidence