Trimethylsilyldiazomethane → 1-Benzyl 3-methyl azetidine-1,3-dicarboxylate

HRID 747012Notes

Reaction equation

HRID 747012 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 109882141-[(Benzyloxy)carbonyl]azetidine-3-carboxylic acid

Product 1

HCID 450725021-Benzyl 3-methyl azetidine-1,3-dicarboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

1-Benzyloxycarbonyl-3-azetidinecarboxylic acid (from step (i); 9.3 g, 39.6 mmol) was dissolved in methanol (100 mL) and toluene (100 mL), and cooled to 0° C. A solution of 2M trimethylsilyldiazomethane in hexanes was then added dropwise until bubbling had ceased and the yellow colour persisted. Acetic acid was then added dropwise until the yellow colour disappeared. Concentration of the solution yielded the title compound as an oil (9.48 g, 38 mmol, 96%).

Workup

  1. customuntil bubbling
  2. additionAcetic acid was then added dropwise until the yellow colour

Sources & evidence

ORD record
ord-68ca3fb969cb4dfdae3d1b10b51885cb
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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