HCID 66652223, compound → HCID 72309435, compound

HRID 418964Notes

Reaction equation

HRID 418964 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.[Li][N:25]=[N+:26]=[N-:27]>CN(C=O)C>[N:25]([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)=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 66652223HCID 66652223, compoundHCID 178506933HCID 178506933, compound

Product 1

HCID 72309435HCID 72309435, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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), LiN3 (0.0213 g, 0.43 mmol), and DMF (1.5 ml) and heat at 90° C. for 3 hours. Cool, add ice and extract with ethyl acetate. Wash organic layer with 3× with water. Dry over anhydrous sodium sulfate and concentrate to a residue which yields after separation on silica gel with 20% EtOAC/hexanes, the titled compound (0.01 g, 34%). 1H NMR (CDCl3) 7.2 (d, J=8.4 Hz, 2H), 6.85 (d, J=8.4 Hz, 2H), 6.73 (s, 1H), 6.68 (s, 1H), 4.35 (s, 2H), 3.45 (m, 1H), 3.15 (m, 1H), 2.95 (m, 1H), 2.85 (m, 1H) 2.55 (m, 1H), 2.25 (m, 1H), 1.7-1.2 (m, 5H). MS m/z 334 (M−1).

Workup

  1. temperatureCool
  2. additionadd ice
  3. extractionextract with ethyl acetate
  4. dry with materialDry over anhydrous sodium sulfate
  5. concentrationconcentrate to a residue which
  6. customyields
  7. customafter separation on silica gel with 20% EtOAC/hexanes

Sources & evidence

ORD record
ord-70cdaefb3b85417cac83739e261b7574
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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