Chloride → (2S)-N-(1,1-Dimethylethyl)piperazine-2-carboxamide

HRID 1586534Notes

Reaction equation

HRID 1586534 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:13]=[N:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-]>CO>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][NH:12][CH2:11][CH2:10][NH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 312ChlorideHCID 4462842N-tert-butylpyrazine-2-carboxamide

Product 1

HCID 9806153(2S)-N-(1,1-Dimethylethyl)piperazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Analogously to Example 4, 5 g (27 mmol) of pyrazinecarboxylic acid tert-butylamide, 127 mg (0.27 mmol) of bicyclo[2.2.1]hepta-2,5-dienerhodium(I) chloride dimer and 353 mg (0.594 mmol) of 1-[1 (R)-(dicyclohexylphosphino)ethyl]-2(S)-(diphenylphosphino)ferrocene were hydrogenated for 20 hours in 70 ml of methanol at 100° C. and 50 bar. A conversion of 85 percent was determined by NMR. The enantiomeric excess (ee) was 49 percent according to GC analysis.

Sources & evidence

ORD record
ord-9c9c268ad2a4414e864801ba4d54cfe8
Source dataset
uspto-grants-1999_08
Patent number
US05945534

Reaction notes

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