HCID 86609131, compound → HCID 86609130, compound

HRID 902343Notes

Reaction equation

HRID 902343 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:19][C:18]3[C:20]([C:25]4[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=4[Cl:32])=[CH:21][C:22]([F:24])=[CH:23][C:17]=3[CH2:16][CH:15]=[CH: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[O:19][C:18]3[C:20]([C:25]4[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=4[Cl:32])=[CH:21][C:22]([F:24])=[CH:23][C:17]=3[CH2:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 86609131HCID 86609131, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86609130HCID 86609130, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A solution (R)-(9-(2,6-dichlorophenyl)-7-fluoro-2,5-dihydrobenzo[b]oxepin-2-yl)methyl 4-methylbenzene-sulfonate (0.7 g, 1.4 mmol) in ethyl acetate/ethanol (10/10 mL) was added platinum (IV) oxide (0.2 g) and the mixture hydrogenated at 45 psi of hydrogen for 14 hours. The reaction mixture was then filtered through celite and the filtrate concentrated under reduced pressure. Chromatography with 10–30% ethyl acetate in hexanes afforded 0.60 g (85%) of (R)-(9-(2,6-dichlorophenyl)-7-fluoro-2,3,4,5-tetrahydrobenzo[b]oxepin-2-yl)methyl 4-methylbenzene-sulfonate as a colorless oil. [α]D25=+24.81° (c=6.6 mg/0.7 mL MeOH); MS (ES) m/z 512.1 ([M+NH4]+).

Workup

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

Sources & evidence

ORD record
ord-25cb45b3b7cc4c439e262cba15a21db5
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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