Hydrochloric Acid → HCID 66652226, compound

HRID 418963Notes

Reaction equation

HRID 418963 reaction equation
[CH3:1][OH:2].Br[CH2:4][C:5]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]2[C:6]=1[CH2:7][CH:8]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH:9]1[CH2:18][CH2:17][CH2:16][CH:10]12.Cl>C(OCC)(=O)C>[OH:25][C:22]1[CH:21]=[CH:20][C:19]([CH:8]2[CH2:7][C:6]3[C:11](=[CH:12][C:13]([OH:15])=[CH:14][C:5]=3[CH2:4][O:2][CH3:1])[CH:10]3[CH2:16][CH2:17][CH2:18][CH:9]23)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66652223HCID 66652223, compound

Product 1

HCID 66652226HCID 66652226, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine Na (0.013 g, 0.53 mmol) and methanol (2 ml) at 0-5° C. and stir until solution forms. Add 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) and stir for 3 hours. Remove solvent in vacuo. Take into ethyl acetate and 1N HCl. Separate organic layer and wash with water. Dry over anhydrous sodium sulfate and remove solvent in vacuo. The residue is chromatographed on silica gel with 25% ethyl acetate/hexanes to yield the titled compound (0.012 g, 37%). 1H NMR (DMSO-d6): 9.16(s, 1H), 9.04 (s, 1H), 7.11 (d, J=7.9 Hz, 2H), 6.71 (d, J=8.8 Hz, 2H), 6.58 (s, 1H), 6.53 (s, 1H), 4.35 (dd, j=16 and 7 Hz, 2H), 3.4 (m, 1H presumed), 3.0 (m, 1H), 2.76 (m, 1H), 2.65 (m, 1H), 2.45(m, 1H) 2.15 (m, 1H), 1.6-1.2 (m, 5H). MS m/z 323 (M−1).

Workup

  1. washSeparate organic layer and wash with water
  2. dry with materialDry over anhydrous sodium sulfate
  3. customremove solvent in vacuo
  4. customThe residue is chromatographed on silica gel with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-95bcc333d6bf4479b30beab4f1508583
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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