Trimethylsilyldiazomethane → (S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

HRID 1020986Notes

Reaction equation

HRID 1020986 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:13](=[O:14])[CH2:12][C@:11]([CH2:18][C:19]([CH3:21])=[CH2:20])([C:15]([OH:17])=[O:16])[CH2:10]1.[Si](C=[N+]=[N-])(C)(C)[CH3:23]>CO>[CH3:23][O:16][C:15]([C@@:11]1([CH2:18][C:19]([CH3:21])=[CH2:20])[CH2:12][C:13](=[O:14])[N:9]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[CH2:10]1)=[O:17]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 58218841(S)-1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid

Product 1

HCID 58218819(S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl esterYield 105.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-1-(2,6-dimethylphenyl)-3-(2-methylallyl)-5-oxo-pyrrolidine-3-carboxylic acid (prepared from c, 430 mg, 1.49 mmol) in MeOH (5 mL) was added TMS-CHN2 (2.24 mL, 4.49 mmol, 2 M solution in hexanes) dropwise. After stirring the yellow colored clear solution at room temperature for 10 min, MeOH was removed under reduced pressure, and the solution was diluted with EtOAc (50 mL) and washed with saturated NaHCO3 solution (25 mL), water (25 mL), brine (25 mL), dried (Na2SO4) and evaporated to obtain (S)-1-(2,6-dimethyl-phenyl)-3-(2-methyl-allyl)-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (474 mg) which was used as such in next step without any further purification. LC-MS: Rt (retention time): 2.14 min, MS: (ES) m/z 302.3 (M+H+).

Workup

  1. customMeOH was removed under reduced pressure
  2. additionthe solution was diluted with EtOAc (50 mL)
  3. washwashed with saturated NaHCO3 solution (25 mL), water (25 mL), brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c79a1ffd03804b20821a427441512110
Source dataset
uspto-grants-2014_05
Patent number
US08716494B2

Reaction notes

Loading…