1-Iodopropane → HCID 58604078, compound

HRID 2113648Notes

Reaction equation

HRID 2113648 reaction equation
[CH2:1]([C:5]12[CH2:20][C:19](=[O:21])[CH:18]=[C:6]1[C:7]1[CH:8]=[CH:9][C:10]([O:14][CH2:15][O:16][CH3:17])=[CH:11][C:12]=1[CH2:13]2)[CH2:2][CH2:3][CH3:4].[CH:22]([N-]C(C)C)([CH3:24])[CH3:23].[Li+].C(I)CC>O1CCCC1.CCOC(C)=O>[CH2:1]([C@@:5]12[C@H:20]([CH2:23][CH2:22][CH3:24])[C:19](=[O:21])[CH:18]=[C:6]1[C:7]1[CH:8]=[CH:9][C:10]([O:14][CH2:15][O:16][CH3:17])=[CH:11][C:12]=1[CH2:13]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 336431-IodopropaneHCID 2724682Lithium diisopropylamideHCID 58604074HCID 58604074, compound

Product 1

HCID 58604078HCID 58604078, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 8a-butyl-6-(methoxymethoxy)-8,8a-dihydrocyclopenta[a]inden-2(1H)-one (109 mg, 0.38 mmol) in anhydrous tetrahydrofuran (THF, 2 mL) was placed under a N2 atmosphere and cooled in an ice bath. Freshly prepared lithium diisopropylamide in THF (1.2 mL of a 0.4M solution, 0.48 mmol) was added and the resulting solution was stirred at 0-5° C. for 25 minutes. Propyl iodide (0.185 in L, 1.9 mmol) was then added and the mixture was stirred overnight with gradual warming to room temperature. The mixture was diluted with EtOAc, washed with 1N HCl, 5% NaHCO3, and brine, dried over MgSO4, filtered, and evaporated under vacuum. The residue (125 mg) was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column, eluting with 19:1 hexane-EtOAc, to afford (rac)-(1S,8aR)-8a-butyl-6-(methoxymethoxy)-1-propyl-8,8a-dihydrocyclopenta[a]inden-2(1H)-one as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. stirringthe mixture was stirred overnight
  3. temperaturewith gradual warming to room temperature
  4. washwashed with 1N HCl, 5% NaHCO3, and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customThe residue (125 mg) was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 12S (1.2×7.5 cm) silica gel column
  9. washeluting with 19:1 hexane-EtOAc

Sources & evidence

ORD record
ord-bed6603ffae349bcbbfe4c38bde9cc23
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

Loading…