Methyl (8-methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetate → HCID 11484351, compound

HRID 1786285Notes

Reaction equation

HRID 1786285 reaction equation
C[O:2][C:3](=[O:14])[CH:4]=[C:5]1[CH2:11][CH:10]2[N:12]([CH3:13])[CH:7]([CH2:8][CH2:9]2)[CH2:6]1.[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[Li]>C1COCC1.[NH4+].[Cl-]>[NH4+:12].[OH-:2].[CH3:13][N:12]1[CH:7]2[CH2:8][CH2:9][CH:10]1[CH2:11][C:5](=[CH:4][C:3]([C:16]1[S:15][CH:19]=[CH:18][CH:17]=1)([C:16]1[S:15][CH:19]=[CH:18][CH:17]=1)[OH:14])[CH2:6]2

Participants

6

Reactant 2

HCID 13670649Methyl (8-methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetateHCID 178418439HCID 178418439, compound

Product 2

HCID 14923Ammonium HydroxideYield 2%HCID 11484351HCID 11484351, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of (8-methyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-acetic acid methyl ester (200 mg, 1.02 mmol) in THF (3 mL) was mixed with 2-thienyllithium (2.02 mL, 1.0 M in THF, 2.02 mmol). The mixture was stirred overnight at r.t., diluted with saturated NH4Cl aqueous solution (20 mL) and extracted with EtOAc. The combined organic phases were dried over MgSO4 and concentrated. Flash chromatography (90% CH2Cl2, 8% CH3OH, 2% NH4OH) then afforded the title compound (132 mg, 39%): LCMS (ES) m/z 332 (M+H)+; 1H-NMR(MeOD) δ 1.35 (m, 1H), 1.61 (m, 1H), 1.81 (m, 1H), 1.95 (m, 1H), 2.12 (m, 3H), 2.29 (s, 3H), 2.37 (m, 1H), 2.68 (m, 1H), 3.03 (m, 1H), 3.22 (m, 1H), 3.32 (s, 1H), 6.15 (s, 1H), 6.95 (m, 4H), 7.30 (m, 2H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4c3711d37de04af6b2801673c3f820ea
Source dataset
uspto-grants-2009_03
Patent number
US07507747B2

Reaction notes

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