Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylate → 1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol

HRID 1724888Notes

Reaction equation

HRID 1724888 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:8]12[CH2:15][CH2:14][C:11]([C:16]([O:18]CC)=O)([CH2:12][CH2:13]1)[CH2:10][CH2:9]2>C1COCC1>[N:8]12[CH2:9][CH2:10][C:11]([C:16]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[OH:18])([CH2:12][CH2:13]1)[CH2:14][CH2:15]2

Participants

4

Reactant 2

HCID 573424Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylateHCID 178506676HCID 178506676, compound

Product 1

HCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanolYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenyllithium (1.5-1.7 M in 70 cyclohexane/30 ether, 20.0 mL, 32 mmol) was chilled down to −30° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (1.51 g, 8.23 mmol) in THF (20 mL) was slowly added to the reaction mixture at −30° C. over 25 min. The reaction was allowed to warm up to room temperature over 16 h. The reaction was quenched with H2O and then evaporated to dryness under vacuum. H2O and EtOAc were added, causing a white solid to crash out. This solid was filtered off, to give the title compound (0.79 g). The aqueous phase was further extracted with EtOAc, the combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The crude product was treated with EtOAc and hexane and filtered to yield more of the title compound (0.67 g). Total yield (1.46 g, 60.7%). EI-MS m/z 294(M+H+) Rt (1.37 min).

Workup

  1. customThe reaction was quenched with H2O
  2. customevaporated to dryness under vacuum
  3. additionH2O and EtOAc were added
  4. filtrationThis solid was filtered off

Sources & evidence

ORD record
ord-fb19e8faa9d5402ebcb7beb0bb077afa
Source dataset
uspto-grants-2009_02
Patent number
US07488827B2

Reaction notes

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