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

HRID 1798443
Notes
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Reaction equation

HRID 1798443 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 10524983(-)-Isopinocampheol

Product 1

HCID 67388677ethyl 4-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yloxy)benzoate

Reagents, catalysts & solvents 2

HCID 83717
Copper iodide
Catalyst
HCID 1140TolueneSolvent

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

  1. customThe reaction mixture was removed
  2. temperaturefrom heat
  3. temperatureto cool
  4. additiondiluted with ethyl acetate
  5. additionpoured into water
  6. washThe organic layer was washed thoroughly with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe crude material was purified by flash chromatography
  11. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes