Tert-butyl (5-fluoro-1-(2-methyl-5-phenylthiazole-4-carbonyl)piperidin-2-yl)methylcarbamate → (2-(Aminomethyl)-5-fluoropiperidin-1-yl)(2-methyl-5-phenylthiazol-4-yl)methanone

HRID 60779Notes

Reaction equation

HRID 60779 reaction equation
[F:1][CH:2]1[CH2:7][N:6]([C:8]([C:10]2[N:11]=[C:12]([CH3:21])[S:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:9])[CH:5]([CH2:22][NH:23]C(=O)OC(C)(C)C)[CH2:4][CH2:3]1>C(Cl)Cl>[NH2:23][CH2:22][CH:5]1[CH2:4][CH2:3][CH:2]([F:1])[CH2:7][N:6]1[C:8]([C:10]1[N:11]=[C:12]([CH3:21])[S:13][C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:9]

Participants

3

Reactant 1

HCID 131737117Tert-butyl (5-fluoro-1-(2-methyl-5-phenylthiazole-4-carbonyl)piperidin-2-yl)methylcarbamate

Product 1

HCID 89739462(2-(Aminomethyl)-5-fluoropiperidin-1-yl)(2-methyl-5-phenylthiazol-4-yl)methanoneYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The above described tert-butyl (5-fluoro-1-(2-methyl-5-phenylthiazole-4-carbonyl)piperidin-2-yl)methylcarbamate was stirred in CH2Cl2 (5 mL) and TFA (5 mL) overnight and concentrated in vacuo. The resulting residue was taken in EtOAc and washed with saturated NaHCO3. EtOAc layer was separated, dried with MgSO4 and concentrated in vacuo to afford desired (2-(aminomethyl)-5-fluoropiperidin-1-yl)(2-methyl-5-phenylthiazol-4-yl)methanone in 42% yield over two steps.

Workup

  1. concentrationTFA (5 mL) overnight and concentrated in vacuo
  2. washwashed with saturated NaHCO3
  3. customEtOAc layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-53bc429da93b45bf8de0c7608383eaee
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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