N-Iodosuccinimide → [1-(5-Iodo-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

HRID 2172960Notes

Reaction equation

HRID 2172960 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[I:17]N1C(=O)CCC1=O>CN(C=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+].O.C(OCC)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1([C:11]2[O:12][C:13]([I:17])=[CH:14][CH:15]=2)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 2

HCID 120273N-IodosuccinimideHCID 67117129tert-Butyl (1-(furan-2-yl)cyclopropyl)carbamate

Product 1

HCID 67115732[1-(5-Iodo-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

To a solution of (1-furan-2-yl-cyclopropyl)-carbamic acid tert-butyl ester (4.30 g, 19.3 mmol) (prepared according to the procedure described in patent application WO 2009/070485 A1) in anhydrous DMF (77 mL) at room temperature is added solid N-iodosuccinimide (4.77 g, 21.2 mmol) in one portion. After 2.5 hours, the reaction is diluted with a saturated aqueous solution of Na2S2O3 (75 mL), water (75 mL), and ethyl ether (100 mL). Phases are separated and the aqueous layer is extracted with ethyl ether (2×100 mL). The combined organic layers are dried over Na2SO4 and concentrated. The resultant solid is triturated with hexanes to afford the title compound as a powder (ES+ m/z 350.5).

Workup

  1. customat room temperature
  2. customPhases are separated
  3. extractionthe aqueous layer is extracted with ethyl ether (2×100 mL)
  4. dry with materialThe combined organic layers are dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resultant solid is triturated with hexanes

Sources & evidence

ORD record
ord-56aa4a1821ba418bbc0b4ee4a9954019
Source dataset
uspto-grants-2015_06
Patent number
US09056858B2

Reaction notes

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