HCID 118007042, compound → 1,1-Dimethylethyl (3S,4R)-3-amino-4-fluoro-1-pyrrolidinecarboxylate

HRID 1486803Notes

Reaction equation

HRID 1486803 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 118007042HCID 118007042, compound

Product 1

HCID 454898861,1-Dimethylethyl (3S,4R)-3-amino-4-fluoro-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3S,4R)-tert-butyl 3-(benzylamino)-4-fluoropyrrolidine-1-carboxylate, 81 (16 mg, 0.054 mmol) was subjected to hydrogenolysis with 10 wt % Pd—C(10 mg) in ethanol (3 ml). The completed reaction mixture was filtered, concentrated and azeotroped with CDCl3 to provide (3S,4R)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate, 83 (8.3 mg, 0.041 mmol, 75.9% yield).

Workup

  1. customThe completed reaction mixture
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. customazeotroped with CDCl3

Sources & evidence

ORD record
ord-536d1f6b547f4d67ab3e1ef13a956598
Source dataset
uspto-grants-2016_08
Patent number
US09428495B2

Reaction notes

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