Hydrochloric Acid → (1S,2S)-1-N-[3-Fluoro-5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride

HRID 1750526Notes

Reaction equation

HRID 1750526 reaction equation
[F:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH:18]C(=O)OC(C)(C)C)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[ClH:26]>O1CCOCC1>[ClH:26].[F:1][C:2]1[C:3]([NH:12][C@H:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[NH2:18])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118308336tert-Butyl N-[(1S,2S)-2-{[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]carbamate

Product 1

HCID 118308208(1S,2S)-1-N-[3-Fluoro-5-(trifluoromethyl)pyridin-2-yl]cyclopentane-1,2-diamine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-{[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]amino}cyclopentyl]carbamate (2.57 g, 7.08 mmol) in 1,4-dioxane (25 ml) was added HCl in 1,4-dioxane (4 M, 20 ml, 80 mmol). The reaction was stirred at room temperature for 20 hours. The reaction mixture was concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. distillationazeotropically distilled with toluene

Sources & evidence

ORD record
ord-5eb204b9a2b04a6c8c2236b5c1d42e37
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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