1,2-Dichloroethane → 3-(Benzyloxy)azetidine hydrochloride

HRID 633899Notes

Reaction equation

HRID 633899 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:12][N:11](C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:26]CCCl.ClC(OC(Cl)C)=O>CO>[ClH:26].[CH2:1]([O:8][CH:9]1[CH2:10][NH:11][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 5213051-Chloroethyl chloroformateHCID 160894483-(Benzyloxy)-1-(diphenylmethyl)azetidine

Product 1

HCID 467370113-(Benzyloxy)azetidine hydrochlorideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A 16 mL vial was charged with 3-(benzyloxy)-1-(diphenylmethyl)azetidine (103 mg, 0.31 mmol; which may be prepared as described in Step 1) and 1,2-dichloroethane (1.4 mL). 1-Chloroethyl chloroformate (45 μL, 0.41 mmol) was added and the reaction mixture was stirred at 70° C. for 1.5 h. After cooling to room temperature, methanol (1.4 mL) was added and the reaction mixture was stirred at 70° C. for 1.5 h. The reaction mixture was cooled and concentrated to dryness. The residue was purified on column chromatography (eluent: Pentane/NH3 7N in MeOH, 98/2) to give the title compound (57 mg, 92%).

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe reaction mixture was stirred at 70° C. for 1.5 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated to dryness
  5. customThe residue was purified on column chromatography (eluent: Pentane/NH3 7N in MeOH, 98/2)

Sources & evidence

ORD record
ord-2b207a3abcef40249eefd6e166628ab1
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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