Methyl iodide → HCID 11002744, compound

Participants

Reaction Steps

To a round-bottom flask equipped with a magnetic stir bar and an addition funnel under N2 was added N-Boc-L-trans-4-hydroxy-proline methyl ester (60 mmol, 1 equiv), P(Ph)3 (72 mmol, 1.2 equiv) and anhydrous THF (275 ml). The solution was cooled to 0 centigrade, DEAD (1.2 equiv) in dry THF was added dropwise; followed by the addition of MeI (1.2 equiv). Upon addition of MeI, the solution turned from dark brown to bright yellow. The reaction mixture was allowed to warm to ambient temperature and stirred for 10 hours. The solvent was removed under reduced pressure and the crude oil was purified by chromatography on silica gel to afford title product (19.44 g) as colorless oil in 91% yield. MS m/e=356.4 [M+H]+.

Provenance & Evidence