Tetrahydrofuran → HCID 58526178, compound

HRID 1184987Notes

Reaction equation

HRID 1184987 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]([N:18]=[C:19]=[N:20][CH:21]([CH3:23])[CH3:22])([CH3:17])[CH3:16].C1C[O:27]CC1>>[OH:11][CH:4]1[CH2:3][C:2]([CH3:12])([CH3:1])[N:7]([O:27][C:19](=[N:20][CH:21]([CH3:23])[CH3:22])[NH:18][CH:15]([CH3:17])[CH3:16])[C:6]([CH3:10])([CH3:9])[CH2:5]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 12734DiisopropylcarbodiimideHCID 137994TempolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 58526178HCID 58526178, compound

Conditions

Temperature
55 °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 diisopropylcarbodiimide (18.6 ml, 120 mmol). The solution is then heated under argon at 55° C. for 6 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 25.8 g of the title compound as a colorless solid, mp. 118-123° 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-36f542082e8c4b988ef16969cf467839
Source dataset
uspto-grants-2014_03
Patent number
US08669398B2

Reaction notes

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