2-Chloroethyl chloroformate → 3-Methanesulfonatoazetidine hydrochloride

HRID 450925Notes

Reaction equation

HRID 450925 reaction equation
[CH3:1][S:2]([O:5][CH:6]1[CH2:9][N:8](C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7]1)(=[O:4])=[O:3].[Cl:23]CCOC(Cl)=O>ClCCl>[ClH:23].[CH3:1][S:2]([O:5][CH:6]1[CH2:9][NH:8][CH2:7]1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

Product 1

HCID 119748813-Methanesulfonatoazetidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(diphenylmethyl)azetidin-3-yl methanesulfonate (WO9725322, p 64), (20 g, 63 mmol) and chloroethylchloroformate (10 mL, 95 mmol) in dichloromethane (100 mL) was heated under reflux for 2.5 hours. The reaction mixture was then concentrated in vacuo and the residue was re-dissolved in methanol (100 mL) and heated under reflux for a further 2.5 hours. The mixture was then cooled to room temperature and concentrated in vacuo to afford the title compound as a white solid in quantitative yield, 9.6 g.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. dissolutionthe residue was re-dissolved in methanol (100 mL)
  5. temperatureheated
  6. temperatureunder reflux for a further 2.5 hours
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86a7a83350754ba989ecf962a6394b55
Source dataset
uspto-grants-2013_07
Patent number
US08486992B2

Reaction notes

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