Pyrrolidine → tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylate

HRID 1005653

反応式

HRID 1005653 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=2[N+:21]([O-])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24]OC(OC)N(C)C.N1CCCC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:15]=2[NH:21][CH:24]=[CH:20]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 601087754-(3-Methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 21070951tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylate収率 26.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-(3-methyl-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (10 g, 31 mmol), N,N-dimethylformamide dimethyl acetal (13.2 mL, 100 mmol) and pyrrolidine (4 mL, 50 mmol) in 45 mL of DMF was heated under reflux for 20 h. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and water. The ethyl acetate was dried and evaporated. The residue was hydrogenated in 200 mL of THF containing 2.5 g of 10% Pd-C at 50 psi for 6 h. The mixture was filtered, concentrated in vacuo, and partitioned between ethyl acetate and aqueous HCl. The ethyl acetate was washed with brine, dried and evaporated. Silica gel chromatography (10% ethyl acetate-hexane) afforded 2.5 g of 4-(1H-Indol-7-yl)-piperazine-1-carboxylic acid tert-butyl ester (19) as a white solid, m.p. 150-151° C.

後処理

  1. temperatureunder reflux for 20 h
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate was dried
  5. customevaporated
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated in vacuo
  8. custompartitioned between ethyl acetate and aqueous HCl
  9. washThe ethyl acetate was washed with brine
  10. customdried
  11. customevaporated

出典と根拠

ORDレコード
ord-159b9b19f9c24f1eb3a2e5b4c77702d4
出典データセット
uspto-grants-2004_09
特許番号
US06787535B2

関連ノート

読み込み中…