Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylate → 1-Azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanol

HRID 1817224Notes

Reaction equation

HRID 1817224 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Li].[N:7]12[CH2:14][CH2:13][C:10]([C:15]([O:17]CC)=O)([CH2:11][CH2:12]1)[CH2:9][CH2:8]2>C1COCC1>[N:7]12[CH2:8][CH2:9][C:10]([C:15]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[OH:17])([CH2:11][CH2:12]1)[CH2:13][CH2:14]2

Participants

4

Reactant 2

HCID 573424Ethyl 1-azabicyclo(2.2.2)octane-4-carboxylateHCID 178418439HCID 178418439, compound2×

Product 1

HCID 688655991-Azabicyclo[2.2.2]oct-4-yl(di-2-thienyl)methanolYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-thienyllithium (1.0 M in THF, 13.0 mL, 13 mmol) was chilled down to −30° C. under Ar. Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (0.77 g, 4.20 mmol) in THF (12 mL) was slowly added to the 2-thienyllithium at −30° C. over 40 min. The reaction was allowed to warm up to room temperature for overnight. The reaction was quenched with H2O and then diluted with EtOAC, hexane and DCM causing a solid to crash out of solution. The solid was filtered off, resulting in the desired compound (0.9132 g, 71.3%). EI-MS m/z 306(M+) Rt (1.33 min).

Workup

  1. customThe reaction was quenched with H2O
  2. additiondiluted with EtOAC, hexane and DCM causing a solid
  3. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-05351a5d381240b592931891273740a8
Source dataset
uspto-grants-2009_10
Patent number
US07598267B2

Reaction notes

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