Sodium Iodide → (S)-3-(m-tolylamino)-1-phenylpropan-1-ol

HRID 1907257Notes

Reaction equation

HRID 1907257 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][C@H:14]([OH:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-].[NH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[CH:32]=1>C(#N)C>[C:33]1([CH3:37])[CH:34]=[CH:35][CH:36]=[C:31]([NH:30][CH2:12][CH2:13][C@@H:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[OH:21])[CH:32]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7934m-ToluidineHCID 11430Potassium CarbonateHCID 11449624(S)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate

Product 1

HCID 58200036(S)-3-(m-tolylamino)-1-phenylpropan-1-olYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the (S)-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate (100 mg, 0.33 mmol) in anhydrous acetonitrile (2 mL) were added K2CO3 (91 mg, 0.66 mmol), NaI (12 mg, 0.0825 mmol) and m-toluidine (42 mg, 0.39 mmol). The mixture was refluxed overnight. The mixture was filtered, and the filter cake was washed with EtOAc. The filtrate was concentrated to give the crude product, which was purified by preparative TLC (3:1 Petroleum ether/EtOAc) to give (S)-3-(m-tolylamino)-1-phenylpropan-1-ol (45 mg, 57%). 1H NMR (400 MHz, CDCl3): δ=2.05 (m, 2H), 2.25 (s, 3H), 3.25 (m, 2H), 3.40 (s, 2H), 4.90 (m, 1H), 6.50 (m, 4H), 7.05 (m, 1H), 7.30 (m, 1H), 7.40 (d, 3H).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. filtrationThe mixture was filtered
  3. washthe filter cake was washed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. customto give the crude product, which
  6. customwas purified by preparative TLC (3:1 Petroleum ether/EtOAc)

Sources & evidence

ORD record
ord-cbbbc380277d44fb96c95b9bb8bfab4e
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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