Sulfuric Acid → (S)-1-(Trifluoroacetyl)piperazine-2-carboxylic acid tert-butylamide sulfuric acid salt

HRID 1419517노트

반응식

HRID 1419517 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].[S:20](=[O:24])(=[O:23])([OH:22])[OH:21]>O1CCCC1.[B-](F)(F)(F)F.C1CC=CCCC=C1.C1CC=CCCC=C1.[Rh]>[S:20](=[O:22])(=[O:21])([OH:24])[OH:23].[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

5

반응물 2

HCID 1118Sulfuric AcidHCID 117479071-Trifluoroacetyl-1,4,5,6-tetra-hydropyrazine-2-carboxylic acid tert-butylamide

생성물 1

HCID 86753988(S)-1-(Trifluoroacetyl)piperazine-2-carboxylic acid tert-butylamide sulfuric acid salt수율 100,730.102%

시약·촉매·용매 2

HCID 5702662Rhodium(1+), bis((1,2,5,6-eta)-1,5-cyclooctadiene)-, tetrafluoroborate(1-) (1:1)촉매HCID 8028Tetrahydrofuran용매

실험 절차

2.50 g (8.95 μmol) of 1-trifluoroacetyl-1,4,5,6-tetrahydropyrazine-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). A solution of 0.89 g (9.08 mmol) of sulfuric acid in 20 ml of degassed tetrahydrofuran was then added. Hydrogenation was then carried out for 18 hours at 200° C. under a hydrogen pressure of 13-10 bar. After distillation of the solvent, 3.42 g (>99%) of the title compound were obtained in the form of a white powder. After cleavage of the protecting groups, the enantioselectivity of the hydrogenation was determined by GC analysis, giving an ee of 79.5 percent. Other data concerning the title compound was:

후처리

  1. distillationAfter distillation of the solvent

출처 및 근거

ORD 기록
ord-6272cec6435642aabd145b7165e171cb
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05886181

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