Iodoethane → HCID 71060332, compound

HRID 1036710Notes

Reaction equation

HRID 1036710 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[CH:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4][NH:3]1.[H-].[Na+].I[CH2:28][CH3:29]>C1COCC1>[CH2:28]([N:3]1[CH2:4][CH:5]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:6]2([CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[C:2]1=[O:1])[CH3:29]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 71060285HCID 71060285, compound

Product 1

HCID 71060332HCID 71060332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 1-oxo-4-phenyl-2,7-diazaspiro[4,5]decane-7-carboxylate (ASW MedChem) (1 g, 3.03 mmol) was dissolved in THF (20 ml) under an atmosphere of nitrogen. The solution was cooled (ice/brine bath) and treated with sodium hydride (60% in oil) (0.133 g, 3.33 mmol). The reaction mixture was stirred for 10 minutes and iodoethane (0.269 ml, 3.33 mmol) was added dropwise. The ice bath was removed and the reaction mixture was stirred at room temperature overnight. The reaction was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title compound. The resulting diastereomeric mixture was used in the next step without further purification.

Workup

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. customThe reaction was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5349896d2a0d406da0bfdcb28aaab826
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

Loading…