Ether hydrochloride → (1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine

HRID 714018Notes

Reaction equation

HRID 714018 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([NH:18]S(C(C)(C)C)=O)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].Cl.CCOCC>CO>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@H:12]([NH2:18])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 86693818N-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 11282264(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Finally, a reaction flask was charged with Compound F in MeOH (10 vol) at 20-25° C. then treated with 2N HCl/Et2O (˜2 mL, 2.0 equiv) and stirred for 12 h. The reaction mixture was concentrated to dryness and the resulting solid was dissolved in water/EtOAc. The aqueous portion was neutralized then extracted with CH2Cl2. The combined organic layers were dried with MgSO4 then concentrated to provide (S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine (Compound B).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. dissolutionthe resulting solid was dissolved in water/EtOAc
  3. extractionThe aqueous portion was neutralized then extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. concentrationthen concentrated

Sources & evidence

ORD record
ord-002a27069d084bf88b05fecf5584c2d0
Source dataset
uspto-grants-2015_11
Patent number
US09187417B2

Reaction notes

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