Triethylamine → (1-Methyl-2-pyrrolidyl)-methyl 3-nitrobenzoate

HRID 586407Notes

Reaction equation

HRID 586407 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].C(N(CC)CC)C.[CH3:20][N:21]1[CH2:25][CH2:24][CH2:23][C@H:22]1[CH2:26][OH:27]>C1COCC1.CN(C1C=CN=CC=1)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:27][CH2:26][CH:22]1[CH2:23][CH2:24][CH2:25][N:21]1[CH3:20])=[O:8])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 643492(2S)-1-Methyl-2-pyrrolidinemethanol

Product 1

HCID 20825661(1-Methyl-2-pyrrolidyl)-methyl 3-nitrobenzoateYield 78.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-nitrobenzoylchloride (2.5 g; 13.5 mmol) in THF (25 ml) was added triethylamine (1.87 ml; 13.5 mmol), a catalytic amount of 4-(N,N-dimethylamino)pyridine and (S)-(−)-1-methyl-2-pyrrolidinemethanol (1.61 ml; 13.5 mmol). The mixture was heated to reflux for 1.5 hours and left with stirring at ambient temperature overnight. The solvent was removed by evaporation and the residue was partitioned between dichloromethane and diluted hydrochloric acid (4 M). The aqueous phase was rendered alkaline by addition of aqueous sodium hydroxide (4 M) and extracted with dichloromethane. The organic extract was dried over sodium sulphate and evaporated to leave 6r (2.8 g; 78%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. waitleft
  4. customThe solvent was removed by evaporation
  5. customthe residue was partitioned between dichloromethane and diluted hydrochloric acid (4 M)
  6. additionby addition of aqueous sodium hydroxide (4 M)
  7. extractionextracted with dichloromethane
  8. extractionThe organic extract
  9. dry with materialwas dried over sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-7b2162daaaa64fa78640768e80081b2d
Source dataset
uspto-grants-2005_08
Patent number
US06936613B2

Reaction notes

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