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

HRID 2038775Notes

Reaction equation

HRID 2038775 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 esterYield 72.7%

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) in anhydrous DMF (77 mL) at room temperature was added N-iodosuccinimide (4.77 g, 21.2 mmol) as a solid in one portion. The reaction was stirred for 2.5 h over which time a deep red color developed. The reaction was diluted with sat. aq. Na2S2O3 (75 mL), water (75 mL), and diethyl ether (100 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (2×100 mL). The combined organic layers were dried over Na2SO4 and concentrated. The resultant solids were triturated with hexanes to give 4.9 g [1-(5-iodo-furan-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester as a light yellow powder, m/z 350.5 [M+H]+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with diethyl ether (2×100 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe resultant solids were triturated with hexanes

Sources & evidence

ORD record
ord-55af917f52c4430ca644bccc249ddb0d
Source dataset
uspto-grants-2013_11
Patent number
US08575360B2

Reaction notes

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