HCID 22135323, compound → HCID 57929708, compound

Participants

Reaction Steps

To a solution of (4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,3-oxazinan-2-one (0.51 g, 2.078 mmol) in DMF (10 mL) at rt under N2 was added KHMDS (0.5 M in toluene, 5 mL) dropwise (gel like precipitation formation) and the mixture was stirred for 10 min. Isopropyl 7-iodoheptanoate (1.24 g, 4.16 mmol, 2 eq) was then added in one portion and the mixture stirred at 65° C. for an additional 5 h and cooled to rt, diluted with water/ether. The layers were separated and the aqueous layer extracted with ether. The organic layers were combined, washed with water and brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and the residue purified by column chromatography (15-30% acetone/toluene) to give desired product isopropyl 7-[(4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-oxo-1,3-oxazinan-3-yl]heptanoate as a colorless oil. 1H NMR (400 MHz, Acetone-d6): δ4.98-4.90 (1H, m), 4.38-4.30 (1 H, m), 4.16-4.12 (1 H, m), 3.83-3.77 (2 H, m), 3.56-3.48 (2 H, m), 3.15-3.07 (1 H, m), 2.26 (2 H, t), 2.11-2.09 (2 H, m), 1.69-1.53 (4 H, m), 1.41-1.27 (4 H, m), 1.21 (6 H, d), 0.92 (9 H, s), 0.12 (6 H, s).

Provenance & Evidence