Ethanol → HCID 67154583, compound

HRID 82999Notes

Reaction equation

HRID 82999 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][C:27]2[O:28][CH:29]=[CH:30][CH:31]=2)[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[O:28]1[CH:29]=[CH:30][CH:31]=[C:27]1[CH2:26][O:25][CH:23]1[CH2:24][NH:21][CH2:22]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 671546031-Benzhydryl-3-(furan-2-ylmethoxy)-azetidine

Product 1

HCID 67154583HCID 67154583, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

1-Chloroethyl chloroformate (534 μL, 4.93 mmol) was added to a solution of 1-benzhydryl-3-(furan-2-ylmethoxy)-azetidine (1.5 g, 4.7 mmol) in dichloromethane (36 mL) at 0° C. The reaction mixture was then heated up to 40° C. and stirred for 2 hours. Ethanol (50 mL) was added and the reaction mixture was stirred for an additional 1 h 30 at 40° C. After concentration to dryness, the crude mixture was triturated in petroleum ether (2×20 mL) to give a yellow oil (558 mg, 74%) which was used in the next step without further purification.

Workup

  1. stirringthe reaction mixture was stirred for an additional 1 h 30 at 40° C
  2. concentrationAfter concentration to dryness
  3. customthe crude mixture was triturated in petroleum ether (2×20 mL)

Sources & evidence

ORD record
ord-f4ab4b53bd8c4d5ca4c81641e9c2a6ad
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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