Ethanol → (E)-3-(2-Methylbut-2-enyloxy)azetidine hydrochloride

HRID 83042Notes

Reaction equation

HRID 83042 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26]/[C:27](/[CH3:30])=[CH:28]/[CH3:29])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[CH3:30]/[C:27](=[CH:28]\[CH3:29])/[CH2:26][O:25][CH:23]1[CH2:24][NH:21][CH2:22]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 67154511HCID 67154511, compound

Product 1

HCID 86672985(E)-3-(2-Methylbut-2-enyloxy)azetidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (107 μL, 1.0 mmol) was added to a solution of (E)-1-benzhydryl-3-(2-methylbut-2-enyloxy)azetidine (290 mg, 0.941 mmol) in dichloromethane (10 mL) at 0° C. The reaction mixture was stirred for 2 hours. Ethanol (10 mL) was then added and the reaction mixture was stirred for an additional 2 hours at 0° C. and 16 hours at room temperature. After concentration to dryness, the crude mixture was triturated in pentane (5 mL) and petroleum ether (5 mL) to afford a colorless oil (211 mg, quantitative).

Workup

  1. stirringthe reaction mixture was stirred for an additional 2 hours at 0° C. and 16 hours at room temperature
  2. concentrationAfter concentration to dryness
  3. customthe crude mixture was triturated in pentane (5 mL)
  4. custompetroleum ether (5 mL) to afford a colorless oil (211 mg, quantitative)

Sources & evidence

ORD record
ord-e1e5a479fc6a4e5bb5e2699150a966b1
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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