O-Methylhydroxylamine hydrochloride → HCID 57314032, compound

Participants

Reaction Steps

(2S,3S,3aS)-2-(3,4-Dimethoxyphenyl)-3a-methoxy-3-methyl-5-n-propyl-2,3,3a,6-tetrahydro-6-methoxyiminobenzofuran was prepared from (2S,3S,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-n-propyl-2,3,3a,6-tetrahydro-6-oxobenzofuran and methoxylamine hydrochloride in pyridine at room temperature for 3 days. The product was purified by flash column chromatography on silica gel (hexane-ethyl acetate, 9:1, v/v) followed by HPLC to afford (2S,3S,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-n-propyl-2,3,3a,6-tetrahydro-6-methoxyiminobenzofuran, n.m.r. (CDCl3): δ0.98 (t, J 7.5 Hz, CH2CH2CH3), 1.11 (d, CH3 --3), 1.64 (m, CH2CH2CH3), 2.52 (m, CH2CH2CH3), 3.0 (s, OCH3), 3.84 (s, Ar--OCH3), 4.04 (s, NOCH3), 5.07 (s, H-2), 5.72 (s, H-7) 6.48 (s, H-4), 6.87-7.12 (m, Ar--H).

Provenance & Evidence