Hydride → HCID 18971567, compound

HRID 2395258Notes

Reaction equation

HRID 2395258 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:15]=[C:16]1[CH2:21][NH:20][CH2:19][CH2:18][NH:17]1.C(O)C.Cl.[H-]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:20]2[CH2:19][CH2:18][NH:17][C:16](=[O:15])[CH2:21]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 166653HydrideHCID 231360Piperazin-2-oneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 21887872Ethanol hydrochloride

Product 1

HCID 18971567HCID 18971567, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-t-butoxycarbonyl-4-oxopiperidine (2.985 g) and 2-oxopiperazine (1.5 g) was dissolved in methanol (25 ml), and molecular sieves 3A (2.5 g) and 1N ethanol-hydrochloric acid (2.5 ml) were then added, followed by stirring for 45 minutes. Cyanoboronsodium hydride (945 ml) was divided into three portions and they were then separately added to the solution under ice-cooling, followed by stirring 5 hours at room temperature. After insolubles were removed with sellaite, the filtrate was then concentrated. To the resultant residue, a saturated sodium hydrogencarbonate solution was added, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated saline solution and then dried over magnesium sulfate. After the solvent was evaporated, the residue was purified by silica gel column chromatography (300 g, chloroform:methanol=30:1 to 10:1) to give 1.448 g of 4-(1-t-butoxycarbonylpiperidin-4-yl)-2-oxopiperazine.

Workup

  1. additionwere then separately added to the solution under ice-
  2. temperaturecooling
  3. stirringby stirring 5 hours at room temperature
  4. customAfter insolubles were removed with sellaite
  5. concentrationthe filtrate was then concentrated
  6. additionTo the resultant residue, a saturated sodium hydrogencarbonate solution was added
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with a saturated saline solution
  9. dry with materialdried over magnesium sulfate
  10. customAfter the solvent was evaporated
  11. customthe residue was purified by silica gel column chromatography (300 g, chloroform:methanol=30:1 to 10:1)

Sources & evidence

ORD record
ord-a45fa5df02504455af43170c252fedc5
Source dataset
uspto-grants-1998_09
Patent number
US05814636

Reaction notes

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