Dimethylamine → HCID 11547212, compound

HRID 1661533Notes

Reaction equation

HRID 1661533 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:31]=[CH:30][C:8]2[C@:9]3([OH:29])[C@@H:14]([OH:15])[CH2:13][C@@H:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C@:10]3([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)[O:11][C:7]=2[CH:6]=1.[CH3:32][NH:33][CH3:34]>>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C@:10]23[C@H:12]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:13][C@H:14]([OH:15])[C@@:9]2([OH:29])[C:8]2[CH:30]=[CH:31][C:5]([O:4][CH2:3][CH2:2][N:33]([CH3:34])[CH3:32])=[CH:6][C:7]=2[O:11]3)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 57545193HCID 57545193, compound

Product 1

HCID 11547212HCID 11547212, compound

Procedure

100 mg (0.22 mmol) of (1S*,3S*,3aR*,8bS*)-6-(2-chloroethoxy)-3a-(4-chlorophenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1,8b-(1H)-diol (Example 48A) are heated in 10 ml of 33% strength ethanolic dimethylamine solution in a closed apparatus at 70° C. under argon overnight. Cooling is followed by concentration. Column chromatography on silica gel 60 (mobile phase: dichloromethane/methanol/triethylamine 95:5:1) results in 89 mg (87% of theory) of the product as racemic mixture.

Workup

  1. temperatureCooling
  2. concentrationis followed by concentration
  3. customColumn chromatography on silica gel 60 (mobile phase: dichloromethane/methanol/triethylamine 95:5:1) results in 89 mg (87% of theory) of the product as racemic mixture

Sources & evidence

ORD record
ord-daa9c7833ec4429ba8695fc711713cbe
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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