3-Quinuclidinone → HCID 53658584, compound

HRID 2274931Notes

Reaction equation

HRID 2274931 reaction equation
COP([CH2:7][C:8]([O:10][CH3:11])=[O:9])(OC)=O.[H-].[Na+].[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C:16](=O)[CH2:15]2>C1COCC1>[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[C:16](=[CH:7][C:8]([O:10][CH3:11])=[O:9])[CH2:15]2

Participants

5

Reactant 3

HCID 195073-QuinuclidinoneHCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetate

Product 1

HCID 53658584HCID 53658584, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(dimethoxyphosphoryl)acetate (2.70 g, 14.8 mmol) in THF (200 ml) at 0° C. was added NaH [60% dispersion in mineral oil] (600 mg, 15.0 mmol). After 1 h of stirring, quinuclidin-3-one (2.00 g, 12.4 mmol) was added and the resultant mixture was stirred at room temperature for 18 h. The reaction was quenched with 50 ml water at 0° C. and the mixture was extracted with EtOAc. The organic layers were combined and concentrated under reduced pressure to afford crude methyl 2-(quinuclidin-3-ylidene)acetate, which was used in next step without purification (1.2 g, 70%).

Workup

  1. customThe reaction was quenched with 50 ml water at 0° C.
  2. extractionthe mixture was extracted with EtOAc
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4dd069f1341e4d4b99d3e23366fe7d41
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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