Isopropyl iodide → HCID 18931349, compound

HRID 1599001Notes

Reaction equation

HRID 1599001 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[C:4]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[NH:3]1.[H-].[Na+].I[CH:23]([CH3:25])[CH3:24]>CN(C=O)C>[O:1]=[C:2]1[N:6]([CH:23]([CH3:25])[CH3:24])[C:5](=[O:7])[C:4]2([CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)[NH:3]1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 3629994Tert-butyl 2,4-dioxo-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 18931349HCID 18931349, compoundYield 13.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of tert-butyl 2,4-dioxo-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (4.18 g, 15.5 mmol), 60% sodium hydride in oil (0.68 g, 17 mmol), and DMF (25 mL) was stirred approximately one hour at 25° C.; then 2-iodopropane (2.7 g, 16 mmol) was added and stirring was continued for three days. The solvent was removed under reduced pressure, and the residue was stirred with water (80 mL) for a few minutes. The insoluble solid was collected and purified by chromatography, eluting with ethyl acetate/hexane (60:40). tert-Butyl 2,4-dioxo-3-(1-methylethyl)-1,3,8-triaza-8-spiro[4.5]decanecarboxylate (0.66 g, 2.1 mmol), m.p. 206°-208° C. was obtained as fine needles.

Workup

  1. stirringstirring
  2. waitwas continued for three days
  3. customThe solvent was removed under reduced pressure
  4. stirringthe residue was stirred with water (80 mL) for a few minutes
  5. customThe insoluble solid was collected
  6. custompurified by chromatography
  7. washeluting with ethyl acetate/hexane (60:40)

Sources & evidence

ORD record
ord-48f3be9953004475bb84f6689f748d90
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

Loading…