HCID 118006851, compound → tert-Butyl (3S,4S)-3-amino-4-fluoropyrrolidine-1-carboxylate

HRID 1486804Notes

Reaction equation

HRID 1486804 reaction equation
C([NH:8][C@@H:9]1[C@@H:13]([F:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:8][C@@H:9]1[C@@H:13]([F:14])[CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1

Participants

4

Reactant 1

HCID 118006851HCID 118006851, compound

Product 1

HCID 45489881tert-Butyl (3S,4S)-3-amino-4-fluoropyrrolidine-1-carboxylateYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3S,4S)-tert-butyl 3-(benzylamino)-4-fluoropyrrolidine-1-carboxylate, 82 (24 mg, 0.082 mmol) was subjected to hydrogenolysis with 10 wt % Pd—C(10 mg) in ethanol (3 ml). The reaction mixture was filtered, concentrated and azeotroped dry with CHCl3 to provide (3S,4S)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate (16.6 mg, 0.081 mmol, 99.2% yield) that was used in the next step without purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customazeotroped
  4. dry with materialdry with CHCl3

Sources & evidence

ORD record
ord-c0f5ae0250044bfe88046e0fa6551547
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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