Methyl Acrylate → methyl 3-azetidin-1-ylpropanoate

HRID 1486944Notes

Reaction equation

HRID 1486944 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[NH:7]1[CH2:10][CH2:9][CH2:8]1>C(Cl)Cl>[N:7]1([CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 10422Azetidine

Product 1

HCID 312726methyl 3-azetidin-1-ylpropanoateYield 66.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl acrylate (2.082 mL, 23.12 mmol) was added to a solution of azetidine (1.2 g, 21.02 mmol) in DCM and the resulting solution stirred at ambient temperature, under an inert atmosphere for 16 h. The reaction mixture was evaporated and the crude product purified by FCC, eluted with 25% EtOAc in DCM, to afford the desired material (2.0 g, 66.5%) as a colourless oil. NMR Spectrum: 1H NMR (400 MHz, CDCl3) δ 1.97-2.1 (2H, m), 2.33 (2H, d), 2.67 (2H, d), 3.18 (4H, t), 3.67 (3H, s).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe crude product purified by FCC
  3. washeluted with 25% EtOAc in DCM

Sources & evidence

ORD record
ord-bc956292645f4517b13f311872fe1a15
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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