Chloride → (S)-(-)-2-t-Butyl-2-piperazinecarboxamide

HRID 1586533

반응식

HRID 1586533 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 9806153(S)-(-)-2-t-Butyl-2-piperazinecarboxamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

0.5 g (2.7 mmol) of pyrazinecarboxylic acid tert-butylamide (prepared according to Example 3), 26.9 mg (58 μmol) of bicyclo[2.2.1]hepta-2,5-dienerhodium(I) chloride dimer and 72 mg (121 μmol) of 1-[1 (R)-(dicyclohexylphosphino)ethyl]-2(S)-(diphenylphosphino)ferrocene were placed in an autoclave under argon. After the addition of 10 ml of degassed methanol, the autoclave was flushed three times with argon and twice with hydrogen. A hydrogen pressure of 50 bar was then applied. Hydrogenation was carried out at 70° C. for 20 hours. The autoclave was depressurized and flushed with nitrogen. The solvent was completely distilled off. The yield of the title compound was 0.50 g. A conversion of 80 percent was determined by NMR. The enantiomeric excess (ee) was 77.6 percent according to GC analysis.

후처리

  1. customthe autoclave was flushed three times with argon
  2. customflushed with nitrogen
  3. distillationThe solvent was completely distilled off

출처 및 근거

ORD 기록
ord-5c436cb535344985a936f615956edea5
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05945534

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