Potassium Formate → (1RS,2SR,6RS,7SR,8RS)-8-[2,6-bis(trifluoromethyl)pyridin-4-yl]-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione

HRID 407859Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH:10]1[C:18](=[O:19])[CH:17]2[CH:12]([CH:13]3[O:20][CH:16]2[CH:15]=[CH:14]3)[C:11]1=[O:21].[F:22][C:23]([F:36])([F:35])[C:24]1[CH:29]=[C:28](Cl)[CH:27]=[C:26]([C:31]([F:34])([F:33])[F:32])[N:25]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C([O-])=O.[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu](I)I>[F:35][C:23]([F:22])([F:36])[C:24]1[CH:29]=[C:28]([CH:15]2[CH2:14][CH:13]3[O:20][CH:16]2[CH:17]2[CH:12]3[C:11](=[O:21])[CH:10]([C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:1])[C:18]2=[O:19])[CH:27]=[C:26]([C:31]([F:32])([F:33])[F:34])[N:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of (1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione (400 mg, 1.4 mmol), 2,6-bis(trifluoromethyl)-4-chloropyridine (531 mg, 1.4 mmol), palladium acetate (16 mg, 0.07 mmol), 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl (67 mg, 0.14 mmol), potassium formate (353 mg, 4.2 mmol), tetrabutylammonium chloride (389 mg, 1.4 mmol) and copper iodide (53 mg, 0.28 mmol) in dry N,N-dimethylformamide (6 ml) are heated, at 150° C. for 30 minutes under microwave irradiation. Purification by preparative reverse-phase HPLC gives (1RS,2SR,6RS,7SR,8RS)-8-[2,6-bis(trifluoromethyl)pyridin-4-yl]-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]decane-3,5-dione.

Workup

customPurification by preparative reverse-phase HPLC

Sources & evidence

ORD record: ord-9a67baad13894d518f2003df3ec2fe47
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754242B2

Reaction notes

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