Methanol → HCID 67154700, compound

HRID 83040Notes

Reaction equation

HRID 83040 reaction equation
[Cl:1]C(OC(Cl)=O)C.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][CH:27]=[CH:28][CH3:29])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>ClC(Cl)C>[ClH:1].[CH2:26]([O:25][CH:23]1[CH2:24][NH:21][CH2:22]1)[CH:27]=[CH:28][CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 67154585HCID 67154585, compound

Product 1

HCID 67154700HCID 67154700, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

1-Chloroethylchloroformate (140 μL, 1.28 mmol) was added to a solution of 1-benzhydryl-3-(but-2-enyloxy)-azetidine (290 mg, 0.98 mmol) in dichloroethane (5 mL) at room temperature. The reaction mixture was then heated up to 70° C. and stirred for 1 hour. After cooling down to room temperature, methanol (5 mL) was added and the reaction mixture was stirred for an additional 1 hour at 70° C. After concentration to dryness, the crude mixture was triturated in pentane (2×15 mL) to give a yellow solid (161 mg, quantitative) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling down to room temperature
  2. stirringthe reaction mixture was stirred for an additional 1 hour at 70° C
  3. concentrationAfter concentration to dryness
  4. customthe crude mixture was triturated in pentane (2×15 mL)
  5. customto give a yellow solid (161 mg, quantitative) which
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-29a82c5a0a6a4f6287697eac66948566
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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