Picolyl chloride → HCID 53947359, compound

HRID 486483Notes

Reaction equation

HRID 486483 reaction equation
[C:1]1([CH2:7][C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Cl>CN(C)C=O>[C:1]1([CH:7]([CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 23393Picolyl chlorideHCID 24758Sodium hydrideHCID 53767445HCID 53767445, compound

Product 1

HCID 53947359HCID 53947359, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (R)-3-quinuclidinyl 2-phenylacetate (see Preparation 9) 1.23 g) and sodium hydride (165 mg of an 80% dispersion in oil) in dimethylformamide (10 ml) was stirred for 1/4 hour, treated with 2-picolyl chloride (0.64 g), stirred for 24 hours then partitioned between ethyl acetate and 10% aqueous potassium carbonate. The organic layer was dried over magnesium sulphate and the residue, after evaporation, was purified by chromatography on silica gel by gradient elution using chloroform plus methanol (0→10%) and aqueous ammonia (0→1%). Appropriate fractions were combined and evaporated to give the title compound as an oil (605 mg, 36%).

Workup

  1. stirringstirred for 24 hours
  2. customthen partitioned between ethyl acetate and 10% aqueous potassium carbonate
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customthe residue, after evaporation
  5. customwas purified by chromatography on silica gel by gradient elution
  6. customevaporated

Sources & evidence

ORD record
ord-3a5be4eb99f24e29a0d73a05f95ebbaf
Source dataset
uspto-grants-1994_03
Patent number
US05292749

Reaction notes

Loading…