Piperonal → HCID 20578938, compound

HRID 1267533Notes

Reaction equation

HRID 1267533 reaction equation
[CH3:1][C:2]([CH3:25])([CH3:24])[CH2:3][C:4]([N:6]([C@H:15]1[CH2:19][NH:18][C@H:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16]1)C1C=CC=C(OC)C=1)=[O:5].[CH:26]1[C:31]([CH:32]=O)=[CH:30][C:29]2[O:34][CH2:35][O:36][C:28]=2[CH:27]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.ClCCCl>[O:36]1[C:28]2[CH:27]=[CH:26][C:31]([CH2:32][N:18]3[CH2:19][C@H:15]([N:6]([C:4](=[O:5])[CH2:3][C:2]([CH3:1])([CH3:25])[CH3:24])[CH2:32][C:31]4[CH:26]=[CH:27][CH:28]=[C:29]([O:34][CH3:35])[CH:30]=4)[CH2:16][C@H:17]3[C:20]([O:22][CH3:23])=[O:21])=[CH:30][C:29]=2[O:34][CH2:35]1

Participants

6

Reactant 3

HCID 8438PiperonalHCID 5003444Sodium cyanoborohydrideHCID 66917787HCID 66917787, compound

Product 1

HCID 20578938HCID 20578938, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of the crude amine (9b) (140 mg) prepared above, piperonal (74 mg, 0.49 mmol) and glacial acetic acid (2 drops) in 1,2-dichloroethane (0.5 mL) was stirred for 30 min at room temperature. 95% Sodium cyanoborohydride (32 mg, 0.48 mmol) was added in small portions and stirring was continued for 1 h. The reaction was quenched with saturated aqueous sodium bicarbonate solution (2 mL), extracted with dichloromethane, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography eluting with dichloromethane-ethyl acetate (90:10-75:25) to give the title pyrrole (10) (115 mg, 71.4%) as a pale yellow oil:

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. customThe reaction was quenched with saturated aqueous sodium bicarbonate solution (2 mL)
  4. extractionextracted with dichloromethane
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with dichloromethane-ethyl acetate (90:10-75:25)

Sources & evidence

ORD record
ord-94c55db0f7994205bcf1b11d8a6eb517
Source dataset
uspto-grants-2003_04
Patent number
US06552016B1

Reaction notes

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