Dimethyl Sulfoxide → HCID 72309404, compound

HRID 418930Notes

Reaction equation

HRID 418930 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]([OH:13])[CH:10]=[C:9]2[C:4]=1[CH2:5][CH:6]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[CH:7]1[CH2:16][CH2:15][CH2:14][CH:8]12.C[N+]([O-:28])(C)C.CS(C)=O.C(Cl)Cl>C(OCC)(=O)C.O>[OH:13][C:11]1[CH:12]=[C:3]([CH:2]=[O:28])[C:4]2[CH2:5][CH:6]([C:17]3[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=3)[CH:7]3[CH2:16][CH2:15][CH2:14][CH:8]3[C:9]=2[CH:10]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1145Trimethylamine oxideHCID 6344DichloromethaneHCID 66652223HCID 66652223, compound

Product 1

HCID 72309404HCID 72309404, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 6-Bromomethyl-4-(4-hydroxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-8-ol (0.037 g, 0.1 mmol), trimethylamine N-oxide (0.03 g, 0.4 mmol), DMSO (1.5 ml), and methylene chloride (0.5 ml) and stir at 0-5° C. for 30 minutes. Add water and ethyl acetate. Wash organic layer 5× with water, dry over anhydrous sodium sulfate and concentrate to a residue which yields after separation on silica gel with 33% EtOAC/hexanes, the titled compound (0.12 g, 39%). 1H NMR (CD3OD) 10.26 (s, 1H), 7.18 (d, J=8.4, Hz, 2H), 7.12 (s, 1H), 6.97 (s, 1H), 6.77 (d, J=7.9 Hz, 2H), 3.4 (m, 1H), 3.15 (m, 1H), 3.0 (m, 2H), 2.55(m, 1H) 2.2 (m, 1H), 1.6-1.2. MS m/z 307 (M−1).

Workup

  1. dry with materialWash organic layer 5× with water, dry over anhydrous sodium sulfate
  2. concentrationconcentrate to a residue which
  3. customyields
  4. customafter separation on silica gel with 33% EtOAC/hexanes

Sources & evidence

ORD record
ord-1351a8c4760a494d8fb1904ca3bf4149
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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