HCID 22388045, compound → HCID 22388242, compound

HRID 1072784Notes

Reaction equation

HRID 1072784 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[C:4]([C:6]1[C:7]([CH3:20])=[CH:8][N:9]2[C:14]=1[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[CH:10]2)=O>O1CCCC1>[Cl:1][C:2]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:3]=1[CH2:4][C:6]1[C:7]([CH3:20])=[CH:8][N:9]2[C:14]=1[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[CH:10]2

Participants

3

Reactant 1

HCID 22388045HCID 22388045, compound

Product 1

HCID 22388242HCID 22388242, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(2,4-dichlorobenzoyl)-2-methylindolizine-7-carboxylate (3.17 g) was dissolved in tetrahydrofuran (32 ml), and a 10M borane-dimethyl sulfide complex (9.5 ml) was dropwise added under ice-cooling. The mixture was stirred at room temperature for 3.5 hr, neutralized and partitioned between ethyl acetate and water. The organic layer was washed three times with water and then with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure to dryness. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=19/1) to give the objective compound (1.81 g) as a pale-yellow oil.

Workup

  1. additiona 10M borane-dimethyl sulfide complex (9.5 ml) was dropwise added under ice-
  2. temperaturecooling
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed three times with water
  5. dry with materialwith saturated brine, dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure to dryness
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=19/1)

Sources & evidence

ORD record
ord-03127084fa5b4a1eabaac26fb93cd54c
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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