Iodine → HCID 90219761, compound

HRID 519242Notes

Reaction equation

HRID 519242 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13](=NN)[CH3:14])([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[I:24]I>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([C:13]([I:24])=[CH2:14])([CH3:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 8471TriethylamineHCID 86727641HCID 86727641, compound

Product 1

HCID 90219761HCID 90219761, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(1-hydrazono-ethyl)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.076 g, 0.33 mmol) and triethylamine (0.169 g, 1.67 mmol) in THF (3 mL) was added dropwise a solution of iodine (0.127 g, 0.50 mmol) in THF (1 mL). The reaction mixture was stirred for 1 h at ambient temperature then concentrated in vacuo. The residue was dissolved in DCM (10 mL) and washed with aqueous Na2S2O3 (5%, 2 mL). The organic phase was separated and concentrated in vacuo. The residue was purified by silica gel chromatography (eluting with 20% EtOAc in petroleum ether) to give 3-(1-iodo-vinyl)-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.060 g, 55%), which was unstable and used without further purification. TLC: Rf=0.30 (eluting with 10% EtOAc in petroleum ether).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM (10 mL)
  3. washwashed with aqueous Na2S2O3 (5%, 2 mL)
  4. customThe organic phase was separated
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (eluting with 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-a248f9a9e72246c4988b2df8cf0dd237
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

Loading…