Ethylenediamine → (Z)-7-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-enoic acid methyl ester

HRID 352407Notes

Reaction equation

HRID 352407 reaction equation
[BH4-].[Na+].C(N)CN.[CH3:7][O:8][C:9](=[O:32])[CH2:10][CH2:11][CH2:12][C:13]#[C:14][CH2:15][N:16]1[CH:21](/[CH:22]=[CH:23]/[C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:19][CH2:18][C:17]1=[O:31].[H][H]>C(O)C.[Ni](Cl)Cl>[CH3:7][O:8][C:9](=[O:32])[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][N:16]1[CH:21](/[CH:22]=[CH:23]/[C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:19][CH2:18][C:17]1=[O:31]

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 4311764Sodium borohydrideHCID 104063027-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-ynoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 11726242(Z)-7-[2-Oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-enoic acid methyl esterYield 43%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 702EthanolSolvent2×

Procedure

A 50 mL round bottom flask was charged with nickel (II) chloride (273 mg, 2.10 mmol) and sodium borohydride (40 mg, 1.05 mmol), then 95% ethanol (2.0 mL) was added. The mixture immediately turned black. After 15 min at rt, ethylene diamine (0.23 mL, 3.36 mmol) was added. After another 15 min at rt, 7-[2-oxo-6-((E)-3-oxo-oct-1-enyl)-piperidin-1-yl]-hept-5-ynoic acid methyl ester (152 mg, 0.42 mmol) in 95% ethanol (2.0 mL) was added via cannula. A hydrogen atmosphere was established by evacuating and refilling with hydrogen (3×) and the reaction mixture was stirred under a balloon of hydrogen for 19 h. The reaction mixture was filtered through celite, washing with ethanol, and the filtrate was concentrated in vacuo. Purification of the resulting residue by flash column chromatography (10→50% EtOAc/CH2Cl2, gradient) afforded 65 mg (43%) of the title compound.

Workup

  1. waitAfter another 15 min at rt
  2. customby evacuating
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashing with ethanol
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the resulting residue by flash column chromatography (10→50% EtOAc/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-caa38115556a4f0c8a6757532b890432
Source dataset
uspto-grants-2004_06
Patent number
US06747037B1

Reaction notes

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