Methanol → 1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate

HRID 1242547Notes

Reaction equation

HRID 1242547 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[N:13][O:14][CH3:15])[CH2:10][CH:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[CH3:21][Si](C=[N+:26]=[N-:27])(C)C>C1(C)C=CC=CC=1>[NH:26]([C:16]([C@@H:9]1[CH2:10][C:11](=[N:13][O:14][CH3:15])[CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:18])[NH2:27].[CH3:15][O:14][N:13]=[C:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C@H:9]([C:16]([O:18][CH3:21])=[O:17])[CH2:10]1

Participants

6

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 72828956tert-butoxycarbonyl-4-(methoxyimino)-2-Pyrrolidinecarboxylic acid2×

Product 2

HCID 585854781-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylateHCID 58714558tert-butyl (2S,4EZ)-2-(hydrazinocarbonyl)-4-(methoxyimino)-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution was made containing, e.g., (4EZ)-1-(tert-butoxycarbonyl)-4-(methoxyimino)-2-pyrrolidinecarboxylic acid (Intermediate 2, 17.81 mmoles; 4.6 gr) in a 1:1 mixture of methanol and toluene (250 mL). Trimethylsilyl diazomethane (32.5 mL of a 2M solution in hexanes, 59 mmol) was then added dropwise to the sirred solution at room temperature under nitrogen. After completion of the evolution of nitrogen gas, the resulting yellow solution was evaporated in vacuo, and the residue re-dissolved in DCM and washed with NH4Clsat and 10% NaHCO3, and brine, dried over Na2SO4 and evaporated in vacuo, giving the desired compound, 1-tert-butyl 2-methyl (2S,4EZ)-4-(methoxyimino)-1,2-pyrrolidinedicarboxylate, as a yellow oil (4.0 g, 83%).

Workup

  1. additionA solution was made containing
  2. customAfter completion of the evolution of nitrogen gas, the resulting yellow solution was evaporated in vacuo
  3. dissolutionthe residue re-dissolved in DCM
  4. washwashed with NH4Clsat and 10% NaHCO3, and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-e96f4efd847e4030a97722e5ca6cca13
Source dataset
uspto-grants-2006_10
Patent number
US07115639B2

Reaction notes

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