Sodium Iodide → HCID 86754629, compound

HRID 1739787Notes

Reaction equation

HRID 1739787 reaction equation
[CH:1](=[C:8]1[CH2:17][CH2:16][C@@H:15]2[C@:10]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=3)([CH2:11][CH2:12][N:13]([CH2:18][CH3:19])[CH2:14]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].[I-].Cl[Si](C)(C)C>C(#N)C>[CH2:1]([C:8]1[CH2:9][C@:10]2([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=3)[C@@H:15]([CH2:16][CH:17]=1)[CH2:14][N:13]([CH2:18][CH3:19])[CH2:12][CH2:11]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 86754628(+/-)-trans-6-Benzylidene-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)isoquinoline

Product 1

HCID 86754629HCID 86754629, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The reaction was conducted as described in Example 10, using 0.93 g (2.6 mmol) of (±)-trans-6-benzylidene-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl4a-(3-methoxyphenyl)isoquinoline, 1.54 g (10.3 mmol) of NaI, 1.3 ml (10.3 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 crystallised from Et2O, yielding 0.09 g of the title compound. M.p.=160-162° C.

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 crystallised from Et2O

Sources & evidence

ORD record
ord-c347fd220db8467294b62ab9a9a932f8
Source dataset
uspto-grants-1999_10
Patent number
US05968949

Reaction notes

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