HCID 86609115, compound → HCID 86609114, compound

HRID 902323Notes

Reaction equation

HRID 902323 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[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=4[Cl:31])[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.C(O)C.[Pt](=O)=O>[CH3:1][C:2]1[CH:7]=[CH:6][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[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=4[Cl:30])[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 86609115HCID 86609115, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86609114HCID 86609114, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution of [(R)-(8-(2,6-dichlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate (0.6 g, 1.25 mmol) in ethyl acetate/ethanol (10/10 mL) was added platinum(IV) oxide (45 mg, 0.198 mmol) and the mixture hydrogenated at 45 psi of hydrogen for 2 hours. The reaction mixture was then filtered through celite and the filtrate concentrated under reduced pressure. Chromatography with 0–15% ethyl acetate in hexanes afforded 0.48 g (80%) of [(R)-8-(2,6-dichlorophenyl)-6-fluorochroman-2-yl]methyl 4-methylbenzenesulfonate as a colorless oil. [α]D25=+9.51° (c 5.3 mg/0.7 mL MeOH); MS (ES) m/z 498.0 ([M+NH4]+).

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-7ca768527e844030ade8e36916e2bf4a
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

Loading…