((2R)-8-(biphenyl-2-yl)-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate → ((2R)-8-(biphenyl-2-yl)-6-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate

HRID 902394Notes

Reaction equation

HRID 902394 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.C(OCC)(=O)C.[Pt](=O)=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 86609153((2R)-8-(biphenyl-2-yl)-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86609155((2R)-8-(biphenyl-2-yl)-6-fluorochroman-2-yl)methyl 4-methylbenzenesulfonateYield 96%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Treatment of ((2R)-8-(biphenyl-2-yl)-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate (1.36 g, 2.79 mmol) with platinum (IV) oxide (84% Pt, 0.35 g) in ethanol (40 mL) and ethyl acetate (10 mL) according to the procedure described for Example 69, Step 8 provided 1.30 g (96%) of ((2R)-8-(biphenyl-2-yl)-6-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate as an off-white solid. MS (ESI) m/z 489.2 ([M+H]+); m/z 506.2 ([M+NH4]+).

Sources & evidence

ORD record
ord-229dc3c1e9cf4b91bfb4d5e0db7b37e0
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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