3-Azidomethyl-1-benzyloxycarbonyl-3-pyrroline → (3S,4R)-3-aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine

HRID 424732노트

반응식

HRID 424732 반응식
[H][H].[N:3]([CH2:6][C@@H:7]1[C@@H:11]([F:12])[CH2:10][N:9]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1)=[N+]=[N-].N(CC1CN(C(OCC2C=CC=CC=2)=O)CC=1)=[N+]=[N-]>C(O)C.[Pt](=O)=O>[NH2:3][CH2:6][C@@H:7]1[C@@H:11]([F:12])[CH2:10][N:9]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:8]1

참가 물질

6

반응물 3

HCID 230620683-Azidomethyl-1-benzyloxycarbonyl-3-pyrrolineHCID 86609601(3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidineHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 66705221(3S,4R)-3-aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine수율 62.7%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 702Ethanol용매2회

실험 절차

Platinum (IV) oxide (50.0 mg) was suspended in ethanol (7 mL) and the suspension was stirred at room temperature under a stream of hydrogen gas (blown by a balloon) for 30 min. Subsequently, a mixture (551 mg) of (3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine and 3-azidomethyl-1-benzyloxycarbonyl-3-pyrroline in ethanol (3 mL) was added and the mixture was stirred at room temperature under a stream of hydrogen gas (blown by a balloon) for 5 hours. The catalyst in the reaction mixture was filtered and was washed with ethanol. The filtrate and the washings were combined and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate->ethyl acetate:methanol=10:1) to give a mixture (313 mg) of (3S,4R)-3-aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine and 3-aminomethyl-1-benzyloxycarbonyl-3-pyrroline.

후처리

  1. customfor 30 min
  2. customfor 5 hours
  3. filtrationThe catalyst in the reaction mixture was filtered
  4. washwas washed with ethanol
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate->ethyl acetate:methanol=10:1)

출처 및 근거

ORD 기록
ord-17502cc700d548f0b0aa2c72994cd2f6
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106072B2

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