Triethylsilane → (2-Fluoro-4,5-dihydroxy-phenyl)-morpholin-4-yl-methanone

HRID 856990Notes

Reaction equation

[F:1][C:2]1[C:3]([C:23]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[O:24])=[CH:4][C:5]2[O:9]C(C3C=CC=CC=3)(C3C=CC=CC=3)[O:7][C:6]=2[CH:22]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:22]=[C:6]([OH:7])[C:5]([OH:9])=[CH:4][C:3]=1[C:23]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (ice-bath) solution of (6-fluoro-2,2-diphenyl-benzo[1,3]dioxol-5-yl)-morpholin-4-yl-methanone (5.70 g, 14.06 mMol) in trifluoroacetic acid (60 ml) was added triethylsilane (2.1 eq, 4.7 ml) over 10 min. The mixture was stirred 20 min at 0° C. and 4 h at room temperature. The volatiles were removed under reduced pressure and the residue purified by column chromatography on silica gel (2:1 ethyl acetate/heptane-ethyl acetate-10:1 ethyl acetate/methanol) to afford (2-fluoro-4,5-dihydroxy-phenyl)-morpholin-4-yl-methanone as liht brown solid (3.19 g, 94%).

Workup

customThe volatiles were removed under reduced pressure
customthe residue purified by column chromatography on silica gel (2:1 ethyl acetate/heptane-ethyl acetate-10:1 ethyl acetate/methanol)

Sources & evidence

ORD record: ord-0c3b20c6806a4126a3a6fc6087034f34
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144890B2

Reaction notes

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