Ethanol → HCID 67154599, compound

HRID 83035Notes

Reaction equation

HRID 83035 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>ClCCl>[ClH:1].[F:31][C:28]([F:29])([F:30])[CH2:27][CH2:26][O:25][CH:23]1[CH2:24][NH:21][CH2:22]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5213051-Chloroethyl chloroformateHCID 67154490HCID 67154490, compound

Product 1

HCID 67154599HCID 67154599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (136 μL, 1.25 mmol) was added to a solution of 1-benzhydryl-3-(3,3,3-trifluoropropoxy)-azetidine (400 mg, 1.19 mmol) in dichloromethane (10 mL) at 0° C. The reaction mixture was stirred for 1 hour. Ethanol (10 mL) was added and the reaction mixture was stirred for 1 hour at room temperature and for 2 hours at 45° C. After concentration to dryness, the crude mixture was triturated in petroleum ether (2×20 mL) to give a yellow oil (245 mg, quantitative) which was used in the next step without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour at room temperature and for 2 hours at 45° C
  2. concentrationAfter concentration to dryness
  3. customthe crude mixture was triturated in petroleum ether (2×20 mL)
  4. customto give a yellow oil (245 mg, quantitative) which
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-7b2033e185444f468190433e48a9adba
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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