Iodine → (2SR,9aRS)-9a-butyl-2-iodo-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7864

Reaction equation

HRID 7864 reaction equation
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([CH3:19])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:20][CH2:21][O:22][CH3:23])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].[Li+].CC([N-]C(C)C)C.[I:32]I>C1COCC1.CCOC(C)=O>[CH2:1]([C:5]12[CH2:17][CH:16]([I:32])[C:15](=[O:18])[C:14]([CH3:19])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:20][CH2:21][O:22][CH3:23])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 219908939a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 67401669(2SR,9aRS)-9a-butyl-2-iodo-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 9a-butyl-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (134 mg, 0.43 mmol) in anhydrous THF (2.5 mL) was cooled in an ice bath, stirred under a nitrogen atmosphere, and treated with 0.4M LDA in THF (1.2 mL, 0.48 mmol). After stirring at 0° C. for 30 minutes, the enolate solution was cooled to −78° C. and treated with a solution of iodine (540 mg, 2.13 mmol) in THF. The resulting mixture was allowed to gradually warm to room temperature, then stirred at room temperature overnight. The mixture was diluted with EtOAc (50 mL), washed with 1N HCl, saturated aqueous Na2SO3 (2×30 mL), water, 5% NaHCO3, and brine, dried over MgSO4, filtered, and evaporated under vacuum to provide crude (2SR,9aRS)-9a-butyl-2-iodo-7-methoxymethoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a gum.

Workup

  1. stirringAfter stirring at 0° C. for 30 minutes
  2. stirringstirred at room temperature overnight
  3. washwashed with 1N HCl, saturated aqueous Na2SO3 (2×30 mL), water, 5% NaHCO3, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-823a4e2ec3744ad0aa61ce7065b5483c
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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