Imidazole → 3-[(4-Chloro-phenyl)-iodo-methyl]-azetidine-1-carboxylic acid tert-butyl ester

HRID 1182108Notes

Reaction equation

HRID 1182108 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.N1C=CN=C1.[C:27]([O:31][C:32]([N:34]1[CH2:37][CH:36]([CH:38]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)O)[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>O1CCCC1.C(#N)C.O1CCCC1>[C:27]([O:31][C:32]([N:34]1[CH2:37][CH:36]([CH:38]([C:40]2[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=2)[I:20])[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 69358918Tert-butyl 3-((4-chlorophenyl)(hydroxy)methyl)azetidine-1-carboxylate

Product 1

HCID 693587933-[(4-Chloro-phenyl)-iodo-methyl]-azetidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22177404Acetonitrile tetrahydrofuranSolvent

Procedure

Polymer supported triphenylphosphine (125 g, 370 mmol) is suspended in tetrahydrofuran: acetonitrile 9:1 (1000 ml) and treated with Iodine (95.2 g, 370 mmol) followed by stirring for 15 minutes. Imidazole (25.5 g, 370 mmol) is added followed by a solution of 3-[(4-Chloro-phenyl)-hydroxy-methyl]-azetidine-1-carboxylic acid tert-butyl ester (44.7 g, 150 mmol) in tetrahydrofuran (150 ml) and the reaction mixture stirred at ambient temperature for 20 hours. The reaction mixture is filtered through celite™ filter material and the filtrate evaporated. The residue is taken up in chloroform and washed with sodium thiosulphate solution, water and brine. The solution is dried over magnesium sulphate and evaporated to provide 3-[(4-Chlorophenyl)-iodo-methyl]-azetidine-1-carboxylic acid tert-butyl ester. 1H NMR 400 MHz, CDCl3, δ 1.35 (9H), 3.21 (1H), 3.37 (1H), 3.60 (2H), 4.05 (1H), 5.12 (1H), 7.20 (4H).

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for 20 hours
  2. filtrationThe reaction mixture is filtered through celite™
  3. filtrationfilter material
  4. customthe filtrate evaporated
  5. washwashed with sodium thiosulphate solution, water and brine
  6. dry with materialThe solution is dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-c72bb778d1f04716854ebc2a05cc8124
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

Loading…