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

HRID 2228750노트

반응식

HRID 2228750 반응식
[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]

참가 물질

5

반응물 1

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

생성물 2

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-1039ccf03b1e4d2fbe3ebc68fc9e303e
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06417203B1

반응 노트

불러오는 중…