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

HRID 424732Notes

Reaction equation

HRID 424732 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-17502cc700d548f0b0aa2c72994cd2f6
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

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