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

HRID 424732ノート

反応式

HRID 424732 の反応式
[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

参加物

6

反応物 3

HCID 230620683-Azidomethyl-1-benzyloxycarbonyl-3-pyrrolineHCID 86609601(3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidineHCID 178418361HCID 178418361、化合物2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-17502cc700d548f0b0aa2c72994cd2f6
出典データセット
uspto-grants-2012_01
特許番号
US08106072B2

反応ノート

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