tert-butyl (2R)-2-(azidomethyl)pyrrolidine-1-carboxylate → Ammonia

HRID 567823ノート

反応式

HRID 567823 の反応式
[N:1]([CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N+]=[N-]>[Pd].C(O)C>[NH3:1].[NH2:1][CH2:4][C@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

参加物

5

反応物 1

HCID 13008760tert-butyl (2R)-2-(azidomethyl)pyrrolidine-1-carboxylate

生成物 2

HCID 222AmmoniaHCID 1512534tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

10% Palladium on charcoal (750 mg) was added to a solution of tert-butyl (2R)-2-(azidomethyl)-1-pyrrolidinecarboxylate (preperation 51)(5.74 g, 25.39 mmol) in ethanol (100 ml). The reaction mixture was hydrogenated @15 psi for 2.5 hrs, after which time the catalyst was filtered off and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (90:10:0.5) as the eluant, to afford the title compound and some starting material. The mixture was dissolved in ethanol (100 ml) and 10% palladium on charcoal (500 mg) was added, the mixture was hydrogenated at 30 psi for 18 hrs, after which time the catalyst was filtered off and the solvent evaporated under reduced pressure to afford the title compound as a clear oil, 4.32 g, (85%).

後処理

  1. customfor 2.5 hrs
  2. filtrationafter which time the catalyst was filtered off
  3. customthe solvent evaporated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-ce99e8d979f744f7833d64da1ac98e6f
出典データセット
uspto-grants-2001_01
特許番号
US06180627B2

反応ノート

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