Methanol → 3-Nitro-5-(2-oxo-piperidin-1-yl)-benzoic acid methyl ester

HRID 852650Notes

Reaction equation

HRID 852650 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:23])[C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[C:8]([NH:15][C:16](=[O:22])[CH2:17][CH2:18][CH2:19][CH2:20]Cl)[CH:7]=1.CO>C1COCC1>[CH3:3][O:4][C:5](=[O:23])[C:6]1[CH:7]=[C:8]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=[O:22])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 693570733-(5-Chloro-pentanoylamino)-5-nitro-benzoic acid methyl ester

Product 1

HCID 693576183-Nitro-5-(2-oxo-piperidin-1-yl)-benzoic acid methyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60% w/w in mineral oil, 680 mg, 17 mmol, 0.9 equiv) was added portionwise to a solution of 3-(5-chloro-pentanoylamino)-5-nitro-benzoic acid methyl ester (D3) (6 g, 19 mmol, 1 equiv) in THF (40 ml) under nitrogen. The resulting mixture was stirred at room temperature for 1 h and then MeOH was added dropwise. The solution was concentrated in vacuo and the residue diluted with AcOEt. The organic phase was washed with H2O, dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (AcOEt/iso-hexane: 1/2) gave 3-nitro-5-(2-oxo-piperidin-1-yl)-benzoic acid methyl ester (B82) (2.8 g, 53%) as a pale orange oil.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. additionthe residue diluted with AcOEt
  3. washThe organic phase was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (AcOEt/iso-hexane: 1/2)

Sources & evidence

ORD record
ord-a70fad6f219f4ff78432b0abcb0922ae
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…