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

HRID 2108792Notes

Reaction equation

HRID 2108792 reaction equation
[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

Participants

6

Reactant 3

HCID 230620683-Azidomethyl-1-benzyloxycarbonyl-3-pyrrolineHCID 86609601(3R,4R)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidineHCID 178418361HCID 178418361, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2f3b2a5d8e8b4fe59e3308b1b80b6237
Source dataset
uspto-grants-2009_04
Patent number
US07514451B2

Reaction notes

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