Sodium Iodide → HCID 59212626, compound

HRID 2178749Notes

Reaction equation

HRID 2178749 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7](O)[CH2:6][CH2:5]2.[CH3:12][C@@H:13]1[NH:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14]1.[Na+].[I-].C(N(CC)CC)C>S(Cl)(Cl)=O.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([N:18]1[CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][C@@H:13]1[CH3:12])[CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 7023035(S)-1-Boc-3-methylpiperazineHCID 134862995-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 59212626HCID 59212626, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

5-Bromo-1-indanol (1.0 g, 4.7 mmol) of Step A was dissolved in thionyl chloride (10 mL). After stirring at room temperature for 2 hrs, the solution was concentrated under vacuum. The residue was taken up in DMF (10 mL). To the mixture were added tert-butyl (3S)-3-methylpiperazine-1-carboxylate (0.94 g, 4.7 mmol), NaI (2 g, 13 mmol) and triethylamine (1.5 mL, 10 mmol). The resulting solution was stirred at 70° C. overnight. After cooling to room temperature, water was added. The solution was extracted with EtOAc twice. The combined EtOAc layers were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica (50% EtOAc in hexane) provided two isomers. Isomer 1 (fast moving isomer): 0.36 g; MS calculated for C19H27BrN2O2 (M+H)+395; found 395.1, 397.0. Isomer 2 (slow moving isomer): 0.33 g; MS found 395.1, 397.0.

Workup

  1. concentrationthe solution was concentrated under vacuum
  2. stirringThe resulting solution was stirred at 70° C. overnight
  3. temperatureAfter cooling to room temperature
  4. extractionThe solution was extracted with EtOAc twice
  5. washThe combined EtOAc layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customColumn chromatography on silica (50% EtOAc in hexane) provided two isomers

Sources & evidence

ORD record
ord-2980ce511a3e4fb9a6d09335951bead8
Source dataset
uspto-grants-2015_06
Patent number
US09067921B2

Reaction notes

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