Hydrochloric Acid → (S)-1-(2-((trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-amine hydrochloride

HRID 535805Notes

Reaction equation

HRID 535805 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][C@H:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22]3)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[ClH:36]>O1CCOCC1>[ClH:36].[F:35][C:2]([F:1])([F:34])[C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([C@@H:15]3[CH2:17][C@H:16]3[NH:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][C@H:23]([NH2:26])[CH2:22]3)=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86673372tert-butyl (S)-1-(2-((trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 67065297(S)-1-(2-((trans)-2-(3'-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-amine hydrochlorideYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a cooled solution of tert-butyl (S)-1-(2-((trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-ylcarbamate (400 mg) in dioxane (5 mL) at 0° C., HCl in 1,4 dioxane (5 mL) was added and stirred for 16 h at RT. The progress of the reaction was monitored by TLC. After completion, the solvent was evaporated, residue was triturated with Et2O to get (S)-1-(2-((trans)-2-(3′-(trifluoromethyl)biphenyl-4-yl)cyclopropylamino)ethyl)pyrrolidin-3-amine hydrochloride (250 mg, 62%) as a white solid.

Workup

  1. customAfter completion, the solvent was evaporated
  2. customresidue was triturated with Et2O

Sources & evidence

ORD record
ord-d89c47a420364927bcbc3fc0f540c25e
Source dataset
uspto-grants-2014_10
Patent number
US08859555B2

Reaction notes

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