O-Methylhydroxylamine hydrochloride → HCID 57314032, compound

HRID 246912Notes

Reaction equation

HRID 246912 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:11]2[C@H:15]([CH3:16])[C@@:14]3([O:25][CH3:26])[CH:17]=[C:18]([CH2:22][CH2:23][CH3:24])[C:19](=O)[CH:20]=[C:13]3[O:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[O:28]([NH2:30])[CH3:29]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:11]2[C@H:15]([CH3:16])[C@@:14]3([O:25][CH3:26])[CH:17]=[C:18]([CH2:22][CH2:23][CH3:24])[C:19](=[N:30][O:28][CH3:29])[CH:20]=[C:13]3[O:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 57308392HCID 57308392, compound

Product 1

HCID 57314032HCID 57314032, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(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).

Workup

  1. customThe product was purified by flash column chromatography on silica gel (hexane-ethyl acetate, 9:1

Sources & evidence

ORD record
ord-017cb073dded402dbd54de15e9e5d192
Source dataset
uspto-grants-1987_11
Patent number
US04704462

Reaction notes

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