Imidazole → HCID 53957647, compound

HRID 581009Notes

Reaction equation

HRID 581009 reaction equation
[C:1]([C:3]1([OH:11])[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1)#[CH:2].N1C=CN=C1.[CH3:17][Si:18](Cl)([CH3:20])[CH3:19].O>CN(C)C=O>[C:1]([C:3]1([O:11][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:8]2[CH2:9][CH2:10][N:5]([CH2:6][CH2:7]2)[CH2:4]1)#[CH:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-ol

Product 1

HCID 53957647HCID 53957647, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Ethynyl-3-hydroxyquinuclidine (1.5 g) and imidazole (1.7 g) were stirred in dimethyl formamide (25 ml). Trimethylsilylchloride (1.35 g) was added slowly to the solution and the mixture was stirred at ambient temperature for 20 hours. The reaction mixture was poured into water (150 ml) and the aqueous phase extracted with ethyl acetate (2×100 ml). The ethyl acetate extracts were combined, washed with water (2×100 ml), brine (100 ml), dried (MgSO4) and evaporated to give 3-ethynyl-3-trimethylsilyloxyquinuclidine as an oil (1.8 g), NMR: 0.15 (9H, s), 1.2-1.38 (1H, m), 1.42-1.6 (1H, m), 1.65-1.9 (3H, m), 2.55-2.7 (4H, m), 2.76 (1H, d), 3.02 (1H, d), 3.55 (1H, s), m/z 224 (M+H).

Workup

  1. extractionthe aqueous phase extracted with ethyl acetate (2×100 ml)
  2. washwashed with water (2×100 ml), brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3ae93dc7a6f14742afc248cd09c773d1
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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