Trimethylsilyldiazomethane → 1-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

HRID 2266697Notes

Reaction equation

HRID 2266697 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:15][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[N:8]1([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH:10]([C:12]([O:14][CH3:15])=[O:13])[CH2:11]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

HCID 446076271-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

1-(t-butoxycarbonyl) azetidine-3-carboxylic acid (1-1)(AXL016917, 1000 mg, 4.97 mmol) was dissolved in MeOH (5 mL)/Toluene (20 mL) and then cooled to 0° C. TMSCHNN (trimethylsilyldiazomethane) (7.45 mmol) was then added drop-wise over 15 minutes with some bubbling observed. The color started clear and slowly turned yellow. The solution was stirred for 10 minutes at 0° C. and then warmed to room temperature over 30 minutes. The solution was then concentrated and pumped on to remove toluene to afford 1.055 g of 1-t-butyl 3-methyl azetidine-1,3-dicarboxylate (1-2) that was used directly in the next step without being purified (99% crude yield).

Workup

  1. temperaturewarmed to room temperature over 30 minutes
  2. concentrationThe solution was then concentrated
  3. customto remove toluene

Sources & evidence

ORD record
ord-7202f5d819f843d1a2bf4bfa870e2f67
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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