rel-(2R,6S)-2,6-dimethylpiperazine → 4-[(cis)-3,5-dimethyl-piperazine-1-carbonyl]-3-methyl-1H-pyrrole-2-carbaldehyde

HRID 1359679Notes

Reaction equation

HRID 1359679 reaction equation
[CH:1]([C:3]1[NH:7][CH:6]=[C:5]([C:8]([OH:10])=O)[C:4]=1[CH3:11])=[O:2].[CH3:12][C@H:13]1[CH2:18][NH:17][CH2:16][C@@H:15]([CH3:19])[NH:14]1>>[CH3:12][C@H:13]1[NH:14][C@@H:15]([CH3:19])[CH2:16][N:17]([C:8]([C:5]2[C:4]([CH3:11])=[C:3]([CH:1]=[O:2])[NH:7][CH:6]=2)=[O:10])[CH2:18]1

Participants

3

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 221354535-Formyl-4-methyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 207615334-[(cis)-3,5-dimethyl-piperazine-1-carbonyl]-3-methyl-1H-pyrrole-2-carbaldehydeYield 88%

Procedure

5-Formyl-4-methyl-1H-pyrrole-3-carboxylic acid (1.00 g, 6.54 mmol) reacted with cis-2,6-dimethylpiperazine (822 mg, 7.19 mmol) to give 1.43 g (88%) of 4-[(3R,5S)-3,5-dimethyl-piperazine-1-carbonyl]-3-methyl-1H-pyrrole-2-carbaldehyde.

Sources & evidence

ORD record
ord-01fdc88499874374ac882d16104659dc
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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