HCID 14612531, compound → HCID 66704817, compound

HRID 2108788Notes

Reaction equation

HRID 2108788 reaction equation
[N:1]([CH2:4][C@@H:5]1[C@H:9]([F:10])[CH2:8][N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[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]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1

Participants

5

Reactant 2

HCID 14612531HCID 14612531, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66704817HCID 66704817, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

(3R,4S)-3-Azidomethyl-1-benzyl-4-fluoropyrrolidine (215 mg) was dissolved in ethanol (3 mL) and platinum (IV) oxide (30.0 mg) was added. The mixture was stirred at room temperature for 5 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 to give (3S,4S)-3-aminomethyl-1-benzyl-4-fluoropyrrolidine as a pale brown oil (191 mg).

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

Sources & evidence

ORD record
ord-d93364962c5145fb8165b1a0d5c0d12f
Source dataset
uspto-grants-2009_04
Patent number
US07514451B2

Reaction notes

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