Diethyl Ether → 1-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

HRID 1774932Notes

Reaction equation

HRID 1774932 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].[CH2:15](Cl)Cl.C[Si](C=[N+]=[N-])(C)C.CCOCC>CO>[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

6

Reactant 4

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 167693TrimethylsilyldiazomethaneHCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

1-(t-butoxycarbonyl)azetidine-3-carboxylic acid (2.03 g, 10.09 mmol) was dissolved in MeOH (10 ml) and DCM (10 mL) and then cooled to 0° C. A 2M solution of trimethylsilyldiazomethane in ether (7.57 ml, 15.1 mmol) was then added drop-wise over 5 minutes. The solution was stirred for 10 minutes at 0° C. and then warmed to room temperature over 30 minutes. The solution was concentrated under reduced pressure to remove volatiles to afford crude 119, which was used directly in the next step without further purification. 1H NMR: 1.44 (s, 9H), 3.35 (m, 1H), 3.75 (s, 3H), 4.10 (d, 4H, J=7.6 Hz).

Workup

  1. temperaturewarmed to room temperature over 30 minutes
  2. concentrationThe solution was concentrated under reduced pressure
  3. customto remove volatiles
  4. customto afford crude 119, which
  5. customwas used directly in the next step without further purification

Sources & evidence

ORD record
ord-8565fc24b86746b7b18fbe32d65dd710
Source dataset
uspto-grants-2016_02
Patent number
US09260434B2

Reaction notes

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