3-[2-Acetyl-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-7-yl]-pyrrole-1-carboxylic acid tert-butyl ester → HCID 59344900, compound

HRID 18196Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][C:10]([C:13]2[C:21]3[O:20][C:19]([C:22](=[O:24])[CH3:23])=[C:18]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=4)[C:17]=3[CH:16]=[C:15]([F:33])[CH:14]=2)=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pt].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[C:21]3[O:20][C:19]([C:22](=[O:24])[CH3:23])=[C:18]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=4)[C:17]=3[CH:16]=[C:15]([F:33])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

3-[2-Acetyl-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-7-yl]-pyrrole-1-carboxylic acid tert-butyl ester (0.114 gm, 0.253 mmol) and platinum (5% on carbon, 0.035 gm) were added to ethyl alcohol (45 ml) and placed under hydrogen (balloon) at 55° C. for two hours. Additional platinum (5% on carbon, 0.065 gm) was added and heated at 60° C. under hydrogen for three hours. The mixture was filtered, concentrated and purified by column chromatography (ethyl acetate/hexane gradient) to give 3-[2-acetyl-5-fluoro-3-(3-fluoro-benzyl)-benzofuran-7-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.096 gm, 83% yield).

Workup

filtrationThe mixture was filtered
concentrationconcentrated
custompurified by column chromatography (ethyl acetate/hexane gradient)

Sources & evidence

ORD record: ord-956227d06b1347048157018b674dba74
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741326B2

Reaction notes

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