Allyl bromide → HCID 86602875, compound

HRID 1517720Notes

Reaction equation

HRID 1517720 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].C1CCN2C(=NCCC2)CC1.[CH2:16]([NH:18][C:19](=[O:21])[O-:20])[CH3:17].[OH:22][C:23]1[C:24]([I:37])=[CH:25][C:26]2[CH:27]([CH2:35]C)[CH:28]3[CH2:32][NH:31][CH2:30][CH:29]3[C:33]=2[CH:34]=1>C(Cl)Cl.O>[CH2:16]([NH:18][C:19](=[O:20])[O-:21])[CH3:17].[CH2:1]([O:22][C:23]1[C:24]([I:37])=[CH:25][C:26]2[CH:27]([CH3:35])[CH:28]3[CH2:32][NH:31][CH2:30][CH:29]3[C:33]=2[CH:34]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86602876HCID 86602876, compound

Product 1

HCID 86602875HCID 86602875, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Allyl bromide (52 μL, 0.6 mmol) and DBU (65 μL, 0.6 mmol) were added to a solution of N-ethylcarbamate-5-hydroxy-6-iodo-8-ethyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (116 mg, 0.3 mmol) in CH2Cl2 (3 mL), and stirred 2 hours at room temperature. The reaction solution was diluted with H2O and filtered through an Extrelut column. The column was washed with CH2Cl2 and the filtrate was concentrated. The crude product was purified via silica plug eluting with Hexanes/EtOAc (3/1, v/v) to afford 50 mg (39%—two steps) of the subtitle compound. MS calculated for C18H22INO3+H: 428, observed: 428.

Workup

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified via silica plug
  5. washeluting with Hexanes/EtOAc (3/1

Sources & evidence

ORD record
ord-f10ae73789b948329169389980f211fc
Source dataset
uspto-grants-2012_07
Patent number
US08232311B2

Reaction notes

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