Sodium Hydroxide → (1R,3S)-1-(4-iodophenyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 445328Notes

Reaction equation

HRID 445328 reaction equation
[I:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[N:7][CH:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:6]2[C:11]3[C:10](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:9][C@H:8]([CH3:16])[NH:7]2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 68501646N-(4-iodobenzylidene)-1-phenylpropan-2-amine

Product 1

HCID 59536378(1R,3S)-1-(4-iodophenyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline

Conditions

Temperature
120 °C

Procedure

To a flask with the crude N-(4-iodobenzylidene)-1-phenylpropan-2-amine (1.17 g) was added trifluoromethanesulfonic acid (6.00 mL, 67805 μmol) and the reaction was heated to 120° C. and stirred 5 h under N2. The reaction was cooled to RT, poured into ice water (20 mL), and basisified with 5 N NaOH (15 mL). The aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organic layers were washed with saturated NaCl (20 mL), dried (MgSO4), and concentrated to give a yellow/brown oil. The residue was purified by ISCO (40 g SiO2, 0-100% EtOAc/hexane) to give (1R,3S)-1-(4-iodophenyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline as a brown oil.

Workup

  1. temperatureThe reaction was cooled to RT
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  3. washThe combined organic layers were washed with saturated NaCl (20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a yellow/brown oil
  7. customThe residue was purified by ISCO (40 g SiO2, 0-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-6f250d8504484f62a073ceeab992fd76
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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