Iodine → HCID 15888168, compound

HRID 1602466Notes

Reaction equation

HRID 1602466 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-5624f454b5ed41d5ac34f0c3ab89fead
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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