1,3-Cyclopentanedione → (S)-Methyl 2-(tert-butoxycarbonylamino)-3-(3-oxocyclopent-1-enyl)propanoate

HRID 2408931Notes

Reaction equation

HRID 2408931 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:5]([O:7][CH3:8])=[O:6])[CH2:3]I.[C:16]1(=O)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17]1>CN(C=O)C.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].II.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[C:12]([O:11][C:9]([NH:1][C@@H:2]([CH2:3][C:16]1[CH2:20][CH2:19][C:18](=[O:21])[CH:17]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

8

Reactant 2

HCID 774661,3-CyclopentanedioneHCID 10903591methyl (2R)-2-(((tert-butoxy)carbonyl)amino)-3-iodopropanoate

Product 1

HCID 69933833(S)-Methyl 2-(tert-butoxycarbonylamino)-3-(3-oxocyclopent-1-enyl)propanoateYield 70%

Reagents, catalysts & solvents 5

HCID 807IodineCatalystHCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalystHCID 6228DimethylformamideSolvent

Procedure

Boc-β-Iodo-Ala-OMe (1.0 g, 3 mmol) was added to a slurry of zinc dust (0.596 g, 9 mmol) and I2 (0.2 mg) in 3 ml DMF under N2. The mixture was stirred for 1 h then Pd2 dba3 (0.070 g, 0.076 mmol), SPhos ligand (0.062 g, 0.15 mmol), and 1,3-cyclopentanedione (0.63 g, 3.9 mmol) were added. The reaction mixture was stirred over night. Purification by flash chromatography (0-100% EtOAc in iso-hexane) gave compound the title compound (0.468 g) in 70% yield. [M+H]+: 284.

Workup

  1. stirringThe reaction mixture was stirred over night
  2. customPurification by flash chromatography (0-100% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-6190ad954f884631a47b1b3850ec2303
Source dataset
uspto-grants-2014_08
Patent number
US08815809B2

Reaction notes

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