Iodine → HCID 66745341, compound

HRID 1961457Notes

Reaction equation

HRID 1961457 reaction equation
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:25]=[CH:24][C:14]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4]CC1.II>CC(C)=O>[O:4]=[C:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:25]=[CH:24][C:14]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 807IodineHCID 66633823HCID 66633823, compound

Product 1

HCID 66745341HCID 66745341, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

tert-butyl 4-(1,4-dioxaspiro[4.5]decan-8-yl)benzylcarbamate (935 mg, 2.6 mmol) was dissolved in acetone (15 ml) together with iodine (68 mg, 0.26 mmol). The mixture was stirred at reflux temperature for 4 hours and at room temperature for 72 hours. The mixture was partially evaporated and then diluted with CH2Cl2 (50 ml). The organic phase was washed with NaHSO3 (50 ml, sat aq), water (50 ml) and brine (50 ml) followed by drying over MgSO4 and evaporation. The product was purified by flash chromatography using pet.ether/EtOAc (3:1) as eluent to give 475 mg (60%) of the title compound as clear syrup.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. customThe mixture was partially evaporated
  3. additiondiluted with CH2Cl2 (50 ml)
  4. washThe organic phase was washed with NaHSO3 (50 ml, sat aq), water (50 ml) and brine (50 ml)
  5. dry with materialby drying over MgSO4 and evaporation
  6. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-38a7eac1f31d45fca19c9be996a58a61
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

Loading…