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

HRID 1419517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419517
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 86753988(S)-1-(Trifluoroacetyl)piperazine-2-carboxylic acid tert-butylamide sulfuric acid saltAusbeute 100.730,102 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

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:

Aufarbeitung

  1. distillationAfter distillation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-6272cec6435642aabd145b7165e171cb
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05886181

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