HCID 14612531, compound → HCID 66704817, compound

HRID 859894Notes

Reaction equation

HRID 859894 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>[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 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

(3R,4S)-3-Azidomethyl-1-benzyl-4-fluoropyrrolidine (215 mg) was dissolved in ethanol (3 mL). To this solution, platinum oxide (IV) (30.0 mg) was added and the mixture was stirred at room temperature for 5 hours in a stream of hydrogen (provided from a balloon). Subsequently, the catalyst was removed from the reaction mixture by filtration through a Celite pad. The removed 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 to obtain 191 mg of (3S,4S)-3-aminomethyl-1-benzyl-4-fluoropyrrolidine as a brown oil.

Workup

  1. customprovided from a balloon)
  2. customSubsequently, the catalyst was removed from the reaction mixture by filtration through a Celite pad
  3. washThe removed catalyst and the Celite pad were washed with ethanol
  4. concentrationthe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e569d1fb93634ea195704e32f6d8968e
Source dataset
uspto-grants-2006_12
Patent number
US07153851B2

Reaction notes

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