Triethylamine → ((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine

HRID 392936Notes

Reaction equation

HRID 392936 reaction equation
[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH:27]([S:30](Cl)(=[O:32])=[O:31])([CH3:29])[CH3:28]>CCCCCC.C(Cl)Cl>[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C@@H:7]([CH3:10])[CH2:8][NH:9][S:30]([CH:27]([CH3:29])[CH3:28])(=[O:32])=[O:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 824082-Propanesulfonyl chlorideHCID 1547949(R)-(+)-beta-Methylphenethylamine

Product 2

HCID 1547949(R)-(+)-beta-MethylphenethylamineHCID 11481889((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amineYield 180.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of the (2R)-2-phenylpropylamine (1.2 g, 8.87 mmol) in hexane (16.0 mL) was added triethylamine (2.47 mL, 17.74 mmol) and is dimethylaminopyridine (0.30 g, 2.47 mmol). Cooled reaction to 5° C., then added a solution of isopropylsulfonyl chloride (0.97 mL, 8.69 mmol) dissolved in methylene chloride (6.0 mL) over a period of 15.0 minutes. Stirred for 45.0 minutes, then stirred at room temperature for 120.0 minutes. Quenched reaction with 1N HCl (20.0 mL) and extracted organic with methylene chloride (25.0 mL). Dried organic layer with anhydrous magnesium sulfate, filtered and concentrated filtrate to provide the final title compound, ((2R)-2-phenylpropyl)[(methylethyl)sulfonyl]amine, (1.93 g, 90.1%) an oil; 1H nmr (CDCl3, 300 MHz) δ 1.25 (d, 3H, J=6.9 Hz), 1.29(d, 3H, J=6.9 Hz), 1.30 (d, 3H, J=7.2 Hz), 2.98 (m, 1H), 3.05 (m, 1H), 3.22 (m, 1H), 3.36 (m, 1H), 3.89 (b, 1H), 7.23 (m, 2H), 7.34 (m, 2H).

Workup

  1. temperatureCooled
  2. customreaction to 5° C.
  3. stirringstirred at room temperature for 120.0 minutes
  4. customQuenched
  5. customreaction with 1N HCl (20.0 mL)
  6. extractionextracted organic with methylene chloride (25.0 mL)
  7. filtrationDried organic layer with anhydrous magnesium sulfate, filtered

Sources & evidence

ORD record
ord-61351087ad0e4e7c8bb28e84a7f0334f
Source dataset
uspto-grants-2004_10
Patent number
US06803484B2

Reaction notes

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