Tetrahydrofuran → HCID 58526172, compound

HRID 1184989Notes

Reaction equation

HRID 1184989 reaction equation
[CH3:1][C:2]1([CH3:12])[N:7]([O])[C:6]([CH3:10])([CH3:9])[CH2:5][CH:4]([OH:11])[CH2:3]1.[H][H].[CH:15]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]([CH3:26])[CH3:25])[C:19]=1[N:27]=[C:28]=[N:29][C:30]1[C:35]([CH:36]([CH3:38])[CH3:37])=[CH:34][CH:33]=[CH:32][C:31]=1[CH:39]([CH3:41])[CH3:40])([CH3:17])[CH3:16].C1C[O:45]CC1>>[CH:36]([C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:39]([CH3:41])[CH3:40])[C:30]=1[NH:29][C:28](=[N:27][C:19]1[C:20]([CH:24]([CH3:26])[CH3:25])=[CH:21][CH:22]=[CH:23][C:18]=1[CH:15]([CH3:17])[CH3:16])[O:45][N:7]1[C:2]([CH3:12])([CH3:1])[CH2:3][CH:4]([OH:11])[CH2:5][C:6]1([CH3:10])[CH3:9])([CH3:38])[CH3:37]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 75100Bis(2,6-diisopropylphenyl)carbodiimideHCID 137994TempolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58526172HCID 58526172, compound

Conditions

Temperature
55 °C

Procedure

4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (5.16 g, 30 mmol) is dissolved in THF (40 ml) and hydrogenated in the presence of 0.08 g Pt (5% on carbon) catalyst using 4 bar hydrogen pressure. The hydrogen uptake stops after approximately one hour. The reaction mixture is then filtered and mixed with the solution of bis(2,6-diisopropylphenyl)carbodiimide (3.8 g, 10.5 mmol) in THF (30 ml). The solution is heated under argon at 55° C. for 6 hours, concentrated, the residue dissolved in dichloromethane (70 ml), washed with water (2×20 ml) and concentrated again. The residue is recrystallized from dichloromethane-ethyl acetate to afford 3.28 g of the title compound as a colorless solid, mp. 174-176° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated
  3. dissolutionthe residue dissolved in dichloromethane (70 ml)
  4. washwashed with water (2×20 ml)
  5. concentrationconcentrated again
  6. customThe residue is recrystallized from dichloromethane-ethyl acetate

Sources & evidence

ORD record
ord-d6f17597e87a4c0bb390e988fbde37f6
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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