Methyl morpholine oxide → HCID 86675858, compound

Participants

Reaction Steps

To (E)-(2S,3S,4R,5R)-3,5-Dimethoxy-2,4-dimethyl-7-tributylstannanyl-hept-6-en-1-ol (100 mg, 0.2 mmol) in anhydrous dichloromethane (2 ml) at room temperature and under an atmosphere of nitrogen was added activated 4A molecular sieves (50 mg), N-methylmorpholine-N-oxide (71 mg, 0.61 mmol) and TPAP (3.6 mg, 0.01 mmol). The reaction was stirred for 30 minutes and filtered through a SiO2 pad, and the pad washed well with diethyl ether. The filtrate was concentrated in vacuo to afford the product as a clear oil (98 mg, 100%). 1H NMR (300 MHz, CDCl3) δ 9.74 (d, J=2.6 Hz, 1H), 6.08 (d, J=19.0 Hz, 1H), 5.58 (dd, J=19.0 Hz, 8.2 Hz, 1H), 3.77 (dd, J=9.1 Hz, 2.3 Hz, 1H), 3.34 (s, 3H), 3.25 (t, J=9.3 Hz, 1H), 3.18 (s, 3H), 2.54 (m, 1H), 1.59 (m, 1H), 1.44 (m, 6H), 1.24 (m, 6H), 0.93 (d, J=7.0 Hz, 3H), 0.82 (m, 15H), 0.75 (d, J=7.0 Hz, 3H).

Provenance & Evidence