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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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4-Formyl-1-trifluoroacetyl-1,4,5,6-tetrahydropyrazine-2-carboxylic acid tert-butylamide → (S)-4-Formyl-1-(trifluoroacetyl)piperazine-2-carboxylic acid tert-butylamide

HRID 1419516
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HRID 1419516 반응식
[C:1]([NH:5][C:6]([C:8]1[N:9]([C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:10][CH2:11][N:12]([CH:14]=[O:15])[CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[B-](F)(F)(F)F.C1CC=CCCC=C1.C1CC=CCCC=C1.[Rh].CC(C)=O>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][N:12]([CH:14]=[O:15])[CH2:11][CH2:10][N:9]1[C:16](=[O:21])[C:17]([F:20])([F:18])[F:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

4

반응물 1

HCID 540332824-Formyl-1-trifluoroacetyl-1,4,5,6-tetrahydropyrazine-2-carboxylic acid tert-butylamide

생성물 1

HCID 53801860(S)-4-Formyl-1-(trifluoroacetyl)piperazine-2-carboxylic acid tert-butylamide수율 99%

시약·촉매·용매 2

HCID 5702662Rhodium(1+), bis((1,2,5,6-eta)-1,5-cyclooctadiene)-, tetrafluoroborate(1-) (1:1)촉매HCID 180Acetone용매

실험 절차

20.6 g (67.0 mmol) of 4-formyl-1-trifluoroacetyl-1,4,5,6-tetrahydropyrazine-2-carboxylic acid tert-butylamide, 26.2 mg (64.5 μmol) of bis(1,5-cyclooctadiene)rhodium(I) tetraflouroborate and 41.8 mg (77 μmol) of 1-[1(R)-(di-tert-butylphospino)ethyl]-2-(S)-(diphenylphosphino)-ferrocene were placed in a 160 ml autoclave under argon (S/C=1000). 70 ml of acetone (degassed) was added and hydrogenation was carried out for 11 hours at 100° C. under a hydrogen pressure of 13-10 bar. After distillation of the solvent, 20.5 g (99%) of the title compound was obtained in the form of a crystalline solid. After cleavage of the protecting groups, the enantioselectivity of the hydrogenation was determined by GC analysis, giving an ee of 96.4 percent. The melting point of the title compound was: 172.0° to 173.0° C. Other data concerning the title compound was:

후처리

  1. distillationAfter distillation of the solvent

출처 및 근거

ORD 기록
ord-7b48e381944c4e38a5c8a21457992445
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05886181

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