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

HRID 424726Notes

Reaction equation

HRID 424726 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)=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 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

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

Workup

  1. filtrationThe catalyst in the reaction mixture was filtered through a Celite pad
  2. washthe catalyst and the Celite pad were washed with ethanol
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluant: ethyl acetate: methanol=10:1)

Sources & evidence

ORD record
ord-ef0f1a71f1d846a481cdbfad1ac4b485
Source dataset
uspto-grants-2012_01
Patent number
US08106072B2

Reaction notes

Loading…