Methanol → HCID 67154642, compound

HRID 82992Notes

Reaction equation

HRID 82992 reaction equation
[Cl:1]C(OC(Cl)C)=O.C([N:21]1[CH2:24][CH:23]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22]1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>ClCCCl>[ClH:1].[CH2:26]([O:25][CH:23]1[CH2:24][NH:21][CH2:22]1)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 67154550HCID 67154550, compound

Product 1

HCID 67154642HCID 67154642, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

1-Chloroethyl chloroformate (180 μL, 1.6 mmol) was added to a solution of 1-benzhydryl-3-butoxyazetidine (370 mg, 1.2 mmol) in 1,2-dichloroethane (6 mL) at room temperature. The reaction mixture was then heated up to 70° C. and stirred for 1.5 hours. After cooling down to room temperature, methanol (7 mL) was added. The reaction mixture was again heated up to 70° C. and stirred for an additional 1.5 hours. After concentration to dryness, the crude mixture was triturated in pentane (2×5 mL) to give a yellow oil (179 mg, 86%) which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling down to room temperature
  2. temperatureThe reaction mixture was again heated up to 70° C.
  3. stirringstirred for an additional 1.5 hours
  4. concentrationAfter concentration to dryness
  5. customthe crude mixture was triturated in pentane (2×5 mL)

Sources & evidence

ORD record
ord-95f30f31f97f486aa7cdaaeb3b3284b4
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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