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

HRID 1419517ノート

反応式

HRID 1419517 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 5702662Rhodium(1+), bis((1,2,5,6-eta)-1,5-cyclooctadiene)-, tetrafluoroborate(1-) (1:1)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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:

後処理

  1. distillationAfter distillation of the solvent

出典と根拠

ORDレコード
ord-6272cec6435642aabd145b7165e171cb
出典データセット
uspto-grants-1999_03
特許番号
US05886181

反応ノート

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