2-Chloroethyl chloroformate → 3-Methanesulfonatoazetidine hydrochloride

HRID 222321Notes

Reaction equation

HRID 222321 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 (WO 97/25322, 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. 1H NMR (400 MHz, DMSO-d6) δ: 3.28 (s, 3H), 4.06 (m, 2H), 4.31 (m, 2H), 5.34 (m, 1H)

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-f6afb962931c467dae98014409aff6e4
Source dataset
uspto-grants-2012_06
Patent number
US08207198B2

Reaction notes

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