Methanol → Methyl 3-fluoroazetidine-3-carboxylate hydrochloride

HRID 1487016Notes

Reaction equation

HRID 1487016 reaction equation
Cl.[F:2][C:3]1([C:7]([OH:9])=[O:8])[CH2:6][NH:5][CH2:4]1.S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[F:2][C:3]1([C:7]([O:9][CH3:14])=[O:8])[CH2:6][NH:5][CH2:4]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 89401641HCID 89401641, compound

Product 1

HCID 89401741Methyl 3-fluoroazetidine-3-carboxylate hydrochloride

Conditions

Temperature
5 °C

Procedure

3-Fluoroazetidine-3-carboxylic acid hydrochloride (0.10 g, 8.4 mmol) was dissolved in methanol (2 mL) and cooled to 5° C. Thionyl chloride (0.05 g, 4.2 mmol) was added dropwise. The reaction mixture was heated at 65° C. overnight and concentrated under reduced pressure to afford methyl 3-fluoroazetidine-3-carboxylate hydrochloride. The product was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated at 65° C. overnight
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4fcdd7d151924fba93baf6b01536fa39
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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