Tert-butyl 3-oxopiperazine-1-carboxylate → HCID 23447455, compound

HRID 1840579Notes

Reaction equation

HRID 1840579 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][NH:33][C:32](=[O:36])[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24].CC(C)([O-])C.[K+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH:17]([N:33]2[CH2:34][CH2:35][N:30]([C:28]([O:27][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:29])[CH2:31][C:32]2=[O:36])[CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 23665647Potassium tert-butoxideHCID 53742494Methyl 3-(1-benzyloxycarbonylpiperidin-4-yl)acrylate

Product 1

HCID 23447455HCID 23447455, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-(1-benzyloxycarbonylpiperidin-4-yl)acrylate (5.55 g) and 4-(tert-butoxycarbonyl)-2-piperazinone (3.66 g) in tetrahydrofuran (50 ml) was added potassium tert-butoxide (0.56 g), and the mixture was stirred under nitrogen atmosphere at room temperature for 3 days. The reaction solution was diluted with ethyl acetate (50 ml), washed with 0.5N hydrochloric acid and saturated brine, dried and concentrated, and the residue was purified with silica gel column chromatography (eluent:acetone/hexane=1/2) to give colorless amorphous of methyl 3-(1-benzyloxycarbonylpiperidin-4-yl)-3-[4-(tert-butoxycarbonyl)-2-oxopiperazine-1-yl]propionate (5.51 g).

Workup

  1. washwashed with 0.5N hydrochloric acid and saturated brine
  2. customdried
  3. concentrationconcentrated
  4. customthe residue was purified with silica gel column chromatography (eluent:acetone/hexane=1/2)

Sources & evidence

ORD record
ord-d9ebbab093df4ab18a6773fb0372a45b
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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