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

HRID 445323

Reaction equation

HRID 445323 reaction equation
FC(F)(F)S(O)(=O)=O.[Br:9][C:10]1[CH:26]=[CH:25][C:13]([CH:14]=[N:15][C@@H:16]([CH3:24])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1.[OH-].[Na+]>>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:14]2[C:19]3[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:17][C@H:16]([CH3:24])[NH:15]2)=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 59536355(S)-N-(4-bromobenzylidene)-1-phenylpropan-2-amine

Product 1

HCID 59536341(1R,3S)-1-(4-bromophenyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline

Conditions

Temperature
120 °C

Procedure

To a flask with trifluoromethanesulfonic acid (3.00 mL, 34 mmol) at 0° C. was added dropwise the (S)—N-(4-bromobenzylidene)-1-phenylpropan-2-amine and the reaction was heated to 120° C. and stirred 19 h under N2. The reaction was poured into ice water (20 mL) and basisified with 5 N NaOH (6 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 (410 mg). 1H-NMR shows 92:8 diastereomeric ratio. The residue was purified by ISCO (40 g SiO2, 0-100% EtOAc/hexane) to give the title compound as a light yellow oil.

Workup

  1. extractionThe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  2. washThe combined organic layers were washed with saturated NaCl (20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-254a242bcc614a32bb12841165b12822
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Linked notes

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