1,10-Phenanthroline → ethyl 4-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yloxy)benzoate

HRID 1798443Notes

Reaction equation

I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][C@H:14]1[C@H:19]([OH:20])[CH2:18][C@@H:17]2[CH2:21][C@H:15]1[C:16]2([CH3:23])[CH3:22].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu](I)I>[CH3:13][C@H:14]1[C@H:19]([O:20][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:18][C@@H:17]2[CH2:21][C@H:15]1[C:16]2([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 120 °C

Procedure

Ethyl 4-iodobenzoate (276 mg), (1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol (154 mg), 1,10-phenanthroline (36 mg), copper iodide (19 mg) and cesium carbonate (652 mg) were combined in toluene (0.5 mL). The reaction was heated to 120° C. over 36 hours. The reaction mixture was removed from heat, allowed to cool, diluted with ethyl acetate and poured into water. The organic layer was washed thoroughly with water and brine, dried over MgSO4, filtered and concentrated under vacuum. The crude material was purified by flash chromatography eluting with 95/5 hexanes/ether.

Workup

customThe reaction mixture was removed
temperaturefrom heat
temperatureto cool
additiondiluted with ethyl acetate
additionpoured into water
washThe organic layer was washed thoroughly with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum
customThe crude material was purified by flash chromatography
washeluting with 95/5 hexanes/ether

Sources & evidence

ORD record: ord-128c9fe2385b4fe09aab780e8c377f6d
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343967B2

Reaction notes

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