Trifluoroacetic acid → (S)-3-amino-1-(pyridin-3-ylmethyl)azepan-2-one

HRID 529501Notes

Reaction equation

HRID 529501 reaction equation
[O:1]=[C:2]1[C@@H:8]([NH:9]C(=O)OC(C)(C)C)[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:9][C@H:8]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68309880(S)-tert-butyl 2-oxo-1-(pyridin-3-ylmethyl)azepan-3-ylcarbamate

Product 1

HCID 68291953(S)-3-amino-1-(pyridin-3-ylmethyl)azepan-2-oneYield 106.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottomed flask, to a stirred solution of (S)-tert-butyl 2-oxo-1-(pyridin-3-ylmethyl)azepan-3-ylcarbamate (150 mg, 0.470 mmol) in DCM (3 mL) was added 2,2,2-trifluoroacetic acid (0.186 mL, 2.35 mmol) at rt under argon. The reaction mixture was stirred at rt for 4 hr. The reaction mixture was concentrated and the residue was dried under vacuum to give (S)-3-amino-1-(pyridin-3-ylmethyl)azepan-2-one (110 mg, 0.502 mmol, 100% yield). Anal. Calcd. for C12H17N3O m/z 219.3. found: 220.3 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-bde349e7df85461c9827c3731e5fbcb6
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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