Hydrochloric Acid → (S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine

HRID 1365488Notes

Reaction equation

HRID 1365488 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@:8]([NH:27][S@@](C(C)(C)C)=O)([C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([F:26])[CH:17]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1.Cl>CO.O1CCOCC1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@:8]([C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:23])[F:24])[CH:19]=[C:18]([F:26])[CH:17]=2)([NH2:27])[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66814189(R)-N-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 59134582(S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(R)-N-((S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-2-methylpropane-2-sulfinamide (0.765 g, 1.53 mmol) was dissolved in anhydrous MeOH (4 mL). At RT, 4.0M HCl in dioxane (1.5 mL) was added and the reaction mixture stirred for 20 min. The reaction mixture was diluted with EtOAc (50 mL), transferred to a separation funnel and washed with 1.0M NaOH (ca. 20 mL). The organic portion was dried over anhydrous Na2SO4, decanted and concentrated yielding (S)-1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethanamine as a pale yellow oil, (0.745 g, crude quantitative yield). LCMS: 1.51 min [M+1] 395.2 (2 min gradient, MeOH/H2O 0.1% TFA).

Workup

  1. customtransferred to a separation funnel
  2. washwashed with 1.0M NaOH (ca. 20 mL)
  3. dry with materialThe organic portion was dried over anhydrous Na2SO4
  4. customdecanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-13bde13d102645608ed677500783cfae
Source dataset
uspto-grants-2011_02
Patent number
US07888376B2

Reaction notes

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