Iodine → HCID 15888168, compound

HRID 1107563Notes

Reaction equation

HRID 1107563 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C@@H:10]3[CH2:12][C@H:11]3[CH2:13][NH:14][C:15](=[O:18])[CH2:16][CH3:17])[C:4]=2[CH2:3][CH2:2]1.[I:19]I>C(O)(=O)C.C(Cl)Cl>[I:19][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[C:9]=1[C@@H:10]1[CH2:12][C@H:11]1[CH2:13][NH:14][C:15](=[O:18])[CH2:16][CH3:17]

Participants

5

Reactant 2

HCID 807IodineHCID 10220503Tasimelteon

Product 1

HCID 15888168HCID 15888168, compoundYield 26.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.12 g (0.6 mmol) (trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cyclopropyl]methyl]propanamide and 0.27 g (0.6 mmol) of lead IV tetraacetate in 1 mL acetic acid was added 0.075 g (0.25 mmol) iodine. The solution was allowed to stir for 1.5 h and was diluted with methylene chloride. The resulting solution was washed with water and saturated sodium bicarbonate solution and dried. The solution was concentrated in vacuo and the residue purified by chromatography on silica eluting with ethyl acetate-hexane, 3:7 containing 0.2% methanol to give the product (25 mg, 11%, mp 148-149° C.).

Workup

  1. washThe resulting solution was washed with water and saturated sodium bicarbonate solution
  2. customdried
  3. concentrationThe solution was concentrated in vacuo
  4. customthe residue purified by chromatography on silica eluting with ethyl acetate-hexane, 3:7 containing 0.2% methanol

Sources & evidence

ORD record
ord-556614ddd792434ba64add2f08fd29a6
Source dataset
uspto-grants-2000_05
Patent number
US06060506

Reaction notes

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