Water → 1-(6-Ethoxy-5-formyl-3-pyridylsulfonyl)-4-ethylpiperazine

HRID 1581741Notes

Reaction equation

HRID 1581741 reaction equation
CC(C[AlH]CC(C)C)C.[CH2:10]([O:12][C:13]1[N:23]=[CH:22][C:21]([S:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH3:34])[CH2:29][CH2:28]2)(=[O:26])=[O:25])=[CH:20][C:14]=1[C:15](OCC)=[O:16])[CH3:11].O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:10]([O:12][C:13]1[N:23]=[CH:22][C:21]([S:24]([N:27]2[CH2:28][CH2:29][N:30]([CH2:33][CH3:34])[CH2:31][CH2:32]2)(=[O:26])=[O:25])=[CH:20][C:14]=1[CH:15]=[O:16])[CH3:11]

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 10109777Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

Product 1

HCID 220522361-(6-Ethoxy-5-formyl-3-pyridylsulfonyl)-4-ethylpiperazineYield 37.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

DIBAL-H (14.8 mL) was added dropwise to a solution of ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinate (5.0 g, 13.5 mmol; prepared as described in WO 99/54333) in toluene (100 mL) at −78° C. under nitrogen. The mixture was held at −78° C. for 1 hour and then water (20 mL) was added dropwise. The mixture was allowed to warm to room temperature and then water (200 mL) and ethyl acetate (200 mL) were added. The organic layer was separated and the aqueous phase re-extracted. The combined organics were washed with brine and concentrated under vacuum to give the product as a brown oil (1.64 g, 36%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase re-extracted
  3. washThe combined organics were washed with brine
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-370e26da004249f68b5383d7fa5ade18
Source dataset
uspto-grants-2004_05
Patent number
US06730786B2

Reaction notes

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