Methanol → Methyl azetidine-3-carboxylate hydrochloride

HRID 1486996Notes

Reaction equation

HRID 1486996 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]([OH:7])=[O:6])[CH2:2]1.S(Cl)([Cl:10])=O.[CH3:12]O>>[ClH:10].[NH:1]1[CH2:4][CH:3]([C:5]([O:7][CH3:12])=[O:6])[CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 931923-azetidinecarboxylic Acid

Product 1

HCID 21100040Methyl azetidine-3-carboxylate hydrochlorideYield 90%

Conditions

Temperature
5 °C

Procedure

A suspension of azetidine-3-carboxylic acid (1 g, 9.8 mmol) in MeOH (10 mL) was cooled to 5° C. Thionyl chloride (5.83 g, 49.45 mmol) was added dropwise maintaining the reaction temperature below 30° C. The mixture was then heated to 65° C. for 10-12 h. The reaction mixture was concentrated under reduced pressure to yield methyl azetidine-3-carboxylate hydrochloride as viscous brown oil (1.3 g, 90%), which was used without further purification.

Workup

  1. temperaturemaintaining the reaction temperature below 30° C
  2. temperatureThe mixture was then heated to 65° C. for 10-12 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-510bdd32a9034157ab5a413ae3f7ecf9
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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