(3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine → benzyl (3S,4S)-3-(aminomethyl)-4-fluoropyrrolidine-1-carboxylate

HRID 859889Notes

Reaction equation

HRID 859889 reaction equation
[N:1]([CH2:4][C@@H:5]1[C@H:9]([F:10])[CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1)=[N+]=[N-].[H][H]>C(O)C.[Pt]=O>[NH2:1][CH2:4][C@@H:5]1[C@H:9]([F:10])[CH2:8][N:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1

Participants

5

Reactant 2

HCID 86600236(3R,4S)-3-azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 66704920benzyl (3S,4S)-3-(aminomethyl)-4-fluoropyrrolidine-1-carboxylateYield 92.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

(3R,4S)-3-Azidomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine (1.35 g) was dissolved in ethanol (30 mL). To this solution, platinum oxide (IV) (190 mg) was added and the mixture was stirred at room temperature for 2 hours in a stream of hydrogen (provided from a balloon). Subsequently, the catalyst was collected from the reaction mixture by filtration through a Celite pad. The collected catalyst and the Celite pad were washed with ethanol. The filtrate and the washing solution were combined and the combined organic layer was concentrated under reduced pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate: methanol=10:1) to give 1.13 g of (3S,4S)-3-aminomethyl-1-benzyloxycarbonyl-4-fluoropyrrolidine as a pale brown oil.

Workup

  1. customprovided from a balloon)
  2. filtrationSubsequently, the catalyst was collected from the reaction mixture by filtration through a Celite pad
  3. washThe collected catalyst and the Celite pad were washed with ethanol
  4. concentrationthe combined organic layer was concentrated under reduced pressure
  5. customThe resulting residue was purified on a silica gel column (eluant=ethyl acetate: methanol=10:1)

Sources & evidence

ORD record
ord-7b21105f6fb24da4a3e11878c6e0d37c
Source dataset
uspto-grants-2006_12
Patent number
US07153851B2

Reaction notes

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