Trifluoroacetic acid → (S)-5-((3-fluoropyrrolidin-1-yl)methyl)pyridin-2-amine

HRID 520498Notes

Reaction equation

HRID 520498 reaction equation
[F:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([NH:14]C(=O)OC(C)(C)C)=[N:12][CH:13]=2)[CH2:3]1.C(O)(C(F)(F)F)=O>ClCCl>[F:1][C@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67993091(S)-tert-butyl 5-((3-fluoropyrrolidin-1-yl)methyl)pyridin-2-ylcarbamate

Product 1

HCID 58552811(S)-5-((3-fluoropyrrolidin-1-yl)methyl)pyridin-2-amineYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 5-((3-fluoropyrrolidin-1-yl)methyl)pyridin-2-ylcarbamate 119 (7.00 g, 23.7 mmol) in dichloromethane (70 mL) was added TFA (15.5 g, 142 mmol). The mixture was stirred for 12 h at room temperature. The solvent was removed in vacuo and sat. aq Na2CO3 was added. The mixture was extracted with dichloromethane, dried (MgSO4) and concentrated to give 120 (4.50 g, 97% yield).

Workup

  1. customThe solvent was removed in vacuo and sat. aq Na2CO3
  2. additionwas added
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0b63a8b1692447a6a669b542d9821e76
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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