Tetrahydrofuran → HCID 58526170, compound

HRID 1184986Notes

Reaction equation

HRID 1184986 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]1([N:21]=[C:22]=[N:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C1C[O:33]CC1>>[CH:24]1([NH:23][C:22](=[N:21][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[O:33][N:7]2[C:2]([CH3:12])([CH3:1])[CH2:3][CH:4]([OH:11])[CH2:5][C:6]2([CH3:10])[CH3:9])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 137994TempolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58526170HCID 58526170, compound

Conditions

Temperature
60 °C

Procedure

4-Hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl (17.25 g, 100 mmol) is dissolved in THF (100 ml) and hydrogenated in the presence of 0.35 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 dicyclohexylcarbodiimide (21.15 g, 102.5 mmol). The solution is then heated under argon at 60° C. for 17 hours, concentrated, diluted with ethyl acetate (40 ml) and allowed to crystallize. The crystals are filtered off, washed with cold ethyl acetate and dried to afford 34.03 g of the title compound as a colorless solid, mp. 157-161° C.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate (40 ml)
  4. customto crystallize
  5. filtrationThe crystals are filtered off
  6. washwashed with cold ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-f1e8c625e9e9430fb44ae318cad33124
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

Loading…