Potassium Iodide → 1-(3-Chloropropyl)-3-(trityloxy)azetidine

HRID 2377185Notes

Reaction equation

HRID 2377185 reaction equation
Cl.[C:2]([O:21][CH:22]1[CH2:25][NH:24][CH2:23]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:35][CH2:36][CH2:37][Cl:38]>CS(C)=O.C(OCC)(=O)C.O>[Cl:38][CH2:37][CH2:36][CH2:35][N:24]1[CH2:23][CH:22]([O:21][C:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:25]1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 219901143-(Trityloxy)azetidine hydrochloride

Product 1

HCID 219900971-(3-Chloropropyl)-3-(trityloxy)azetidine

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 5 mL of dimethyl sulfoxide was dissolved 0.50 g of 3-(trityloxy)azetidine hydrochloride, and to the solution were added 0.49 g of potassium carbonate, 0.35 g of potassium iodide and 0.22 mL of 1-bromo-3-chloropropane, after which the resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture were added 15 mL of water and 10 mL of ethyl acetate, and the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1-(3-chloropropyl)-3-(trityloxy)azetidine.

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d65c6c9735734f60bd86625abe9810ec
Source dataset
uspto-grants-2008_12
Patent number
US07468443B2

Reaction notes

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