Hydrogen Peroxide → HCID 56646611, compound

Participants

Reaction Steps

To a solution of 3-((R)-2-Allyl-5-cyclohexyl-3-oxo-morpholin-4-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (200 mg, 0.45 mmol, 1.0 equiv) in THF (4.0 mL) at 0° C. was added 9-BBN (2.2 mL, 0.5 M in THF, 1.1 mmol, 2.5 equiv) over 10 minutes and the resulting solution was stirred at room temperature for 18 hours. The solution was then cooled to 0° C. and to the solution was added EtOH, aq. NaOH. solution, aq. H2O2 solution. The reaction mixture was heated to reflux for 90 minutes. After cooled to room temperature, the reaction mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and the residue was purified by prep-HPLC to give product 3-[(2R,5R)-5-Cyclohexyl-2-(3-hydroxy-propyl)-3-oxo-morpholin-4-yl]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid (20 mg) and 3-[(2S,5R)-5-Cyclohexyl-2-(3-hydroxy-propyl)-3-oxo-morpholin-4-yl]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid (20 mg). The stereochemistry at 2 position of morpholinone has not been established. Product 1: MW: 448.3 [M+H]+. 1H-NMR (400 MHz, CD3OD): δ 6.93 (s, 1H), 4.14 (m, 1H), 4.0 (m, 1H), 3.62 (m, 1H), 3.58 (m, 2H), 2.02-1.48 (m, 10H), 1.32 (s, 9H), 1.25-1.17 (m, 6H). Product 2: MW: 448.3 [M+H]+. 1H-NMR (400 MHz, CD3OD): δ 6.97 (s, 1H), 4.13 (m, 1H), 3.90 (m, 1H), 3.82 (m, 1H), 3.57 (m, 2H), 1.97-1.48 (m, 10H), 1.32 (s, 9H), 1.26-1.09 (m, 6H).

Provenance & Evidence