Sodium Iodide → HCID 86754627, compound

HRID 1739785Notes

Reaction equation

HRID 1739785 reaction equation
[CH2:1]([N:3]1[CH2:12][CH2:11][C@@:10]2([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=3)[C@@H:5]([CH2:6][CH:7]=[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:9]2)[CH2:4]1)[CH3:2].[Na+].[I-].Cl[Si](C)(C)C>C(#N)C>[CH2:1]([N:3]1[CH2:12][CH2:11][C@@:10]2([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[C@@H:5]([CH2:6][CH:7]=[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:9]2)[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 86754626(+/-)-trans-2-Ethyl-4a-(3-methoxyphenyl)-6-phenyl-1,2,3,4,4a,5,8,8a-octahydroisoquinoline

Product 1

HCID 86754627HCID 86754627, compoundYield 15.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction was conducted as described in Example 10, using 0.77 g (2.2 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-phenyl-1 ,2,3,4,4a,5,8,8a-octahydroisoquinoline, 1.32 g (8.8 mmol) of NaI, 1.1 ml (8.8 mmol) of chlorotrimethylsilane and 20 ml of acetonitrile. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 90:7:0.7 respectively. The resulting solid was triturated in acetone, yielding 0.115 g of the title compound. M.p.=215-218° C. C23H27NO

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash chromatography
  3. washeluting with a mixture CH2Cl2 /MeOH/conc
  4. customThe resulting solid was triturated in acetone

Sources & evidence

ORD record
ord-6675426e0fda415683407b8c7deca592
Source dataset
uspto-grants-1999_10
Patent number
US05968949

Reaction notes

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