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

HRID 1419518ノート

反応式

HRID 1419518 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]>[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]

参加物

4

反応物 1

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

生成物 1

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

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 8857Ethyl Acetate溶媒

実験手順

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:

後処理

  1. distillationAfter distillation of the solvent

出典と根拠

ORDレコード
ord-c0b754a4d62749dabd5625c3a4a38434
出典データセット
uspto-grants-1999_03
特許番号
US05886181

反応ノート

読み込み中…