Allyl bromide → HCID 70087875, compound

Participants

Reaction Steps

Analogously to the procedure of Example 3, the title compound was prepared from 0.79 g (3 mmol) of the compound from Example 7, 3 ml of 1 molar lithium bis(trimethylsilyl)-amide solution in THF and 0.36 g (3 mmol) of allyl bromide in 10 ml of THF. Chromatographic purification was carried out using a mixture of dichloromethane and petroleum ether (40-60) in a ratio of 100:4. Yield: 684 mg (74.8%) of a pale yellow oil; Diastereomeric purity: >99% de (HPLC). MS (DCI/NH3) [m/e]: 322 (100, M+NH4+) 1H-NMR (200 MHz; CDCl3): δ[ppm]=2.24 (dd,1H); 2.37 (dd,1H), 2.72 (m,2H), 3.16 (d,1H), 3.28 (d,1H), 3.48(m,1H), 5.03 (dd,1H), 5.05 (m,1H), 5.12 (dd,1H), 5.78 (ddt,1H), 5.89 (m,1H), 6.04 (m,1H), 7.4-7.5 (br m,3H), 7.75 (s,1H), 7.8 (m,3H)

Provenance & Evidence