1-Trifluoroacetyl-1,4,5,6-tetra-hydropyrazine-2-carboxylic acid tert-butylamide → (S)-1-(Trifluoroacetyl)piperazine-2-carboxylic acid tert-butylamide

HRID 1419518노트

반응식

HRID 1419518 반응식
[C:1]([NH:5][C:6]([C:8]1[N:9]([C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[CH2:10][CH2:11][NH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[B-](F)(F)(F)F.C1CC=CCCC=C1.C1CC=CCCC=C1.[Rh].C(OCC)(=O)C>[C:1]([NH:5][C:6]([C@@H:8]1[CH2:13][NH:12][CH2:11][CH2:10][N:9]1[C:14](=[O:19])[C:15]([F:18])([F:16])[F:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 117479071-Trifluoroacetyl-1,4,5,6-tetra-hydropyrazine-2-carboxylic acid tert-butylamide

생성물 1

HCID 54528768(S)-1-(Trifluoroacetyl)piperazine-2-carboxylic acid tert-butylamide수율 99.3%

시약·촉매·용매 2

HCID 5702662Rhodium(1+), bis((1,2,5,6-eta)-1,5-cyclooctadiene)-, tetrafluoroborate(1-) (1:1)촉매HCID 8857Ethyl Acetate용매

실험 절차

250 g (8.95 mmol) of 1-trifluoroacetyl-1,4,5,6-tetra-hydropyrazine-2-carboxylic acid tert-butylamide, 7.5 mg (18 μmol) of bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate and 11.5 mg (21 μmol) of 1-[1(R)-(di-tert-butylphosphino)ethyl]-2(S)-(diphenylphosphino)ferrocene were placed in a 50 ml autoclave under argon (educt:catalyst=486). 20 ml of degassed ethyl acetate was added and hydrogenation was carried out for 18 hours at 90° C. under a hydrogen pressure of 13-10 bar. After distillation of the solvent, 2.50 g of the crude title compound was obtained in the form of a light yellow powder. After cleavage of the protecting groups, the enantioselectivity of the hydrogenation was determined by GC analysis, giving an ee of 47.2 percent. Other data concerning the title compound was:

후처리

  1. distillationAfter distillation of the solvent

출처 및 근거

ORD 기록
ord-c0b754a4d62749dabd5625c3a4a38434
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886181

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