Chloroform → HCID 86754621, compound

HRID 1739780Notes

Reaction equation

HRID 1739780 reaction equation
[CH:1](=[C:8]1[CH2:17][C@@H:16]2[C@:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25]C)[CH:20]=3)([CH2:12][CH2:13][N:14]([CH3:18])[CH2:15]2)[CH2:10][C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br.C(Cl)(Cl)[Cl:33]>>[ClH:33].[CH:1](=[C:8]1[CH2:17][C@@H:16]2[C@:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=3)([CH2:12][CH2:13][N:14]([CH3:18])[CH2:15]2)[CH2:10][C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 25134Boron tribromideHCID 86754620HCID 86754620, compound

Product 1

HCID 86754621HCID 86754621, compound

Procedure

The reaction was conducted as described in Example 3, using 0.1 g (0.28 mmol) di (±)-trans-7-benzylidene-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-methyl-4a-(3-methoxyphenyl)-6-isoquinolinone, 0.16 ml (1.7 mmol) of boron tribromide and 6 ml of dry CHCl3. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 86:10:0.6 respectively. The resulting solid was dissolved in MeOH and the solution brought to acidic pH with Et2O/HCl. The solvent was removed in vacuo, the resulting solid was triturated with acetone, yielding 0.07 g of the title compound. M.p.=256-260° C.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash chromatography
  3. washeluting with a mixture CH2Cl2 /MeOH/conc
  4. dissolutionThe resulting solid was dissolved in MeOH
  5. customThe solvent was removed in vacuo
  6. customthe resulting solid was triturated with acetone

Sources & evidence

ORD record
ord-c7813ca8e38a4ddaa955d3427c6dad61
Source dataset
uspto-grants-1999_10
Patent number
US05968949

Reaction notes

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