Triethylamine → 1-Azetidinecarboxylic acid, 2-methyl-3-oxo-, 1,1-dimethylethyl ester

HRID 519092Notes

Reaction equation

[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]([CH3:14])[C:9](=[O:13])[CH:10]=[N+]=[N-])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC>C(Cl)Cl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:7]1[CH2:10][C:9](=[O:13])[CH:8]1[CH3:14])=[O:15])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

(3-Diazo-1-methyl-2-oxo-propyl)-carbamic acid tert-butyl ester (0.250 g, 1.17 mmol) was dissolved in anhydrous DCM (6 mL) and Et3N (1.18 mg, 0.012 mmol) was added. The reaction mixture was cooled to 0° C. and rhodium (II) acetate (0.010 g, 0.023 mmol) was added. The reaction mixture was stirred at 0° C. for 1 h then concentrated in vacuo to give 2-methyl-3-oxo-azetidine-1-carboxylic acid tert-butyl ester, which was used in the next step without further purification. TLC (eluting with 20% EtOAc/heptane) Rf=0.3.

Workup

concentrationthen concentrated in vacuo

Sources & evidence

ORD record: ord-7f93eece9d644fbc8fdf13f5ad91e0fd
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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