1,2-Dibromoethane → HCID 66886139, compound

HRID 1863973Notes

Reaction equation

HRID 1863973 reaction equation
BrCCBr.[Mg].Br[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][CH2:15][C@@H:16]([CH3:20])[CH2:17][O:18][CH3:19])=[CH:9][CH:8]=1.[CH2:21]([N:28]1[CH2:33][CH2:32][C:31](=[O:34])[CH:30]([CH2:35][O:36][C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:21]([N:28]1[CH2:33][CH2:32][C:31]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14][CH2:15][C@@H:16]([CH3:20])[CH2:17][O:18][CH3:19])=[CH:9][CH:8]=2)([OH:34])[CH:30]([CH2:35][O:36][C:37]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:29]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 5462224Magnesium2×HCID 155469291-Benzyl-3-[(triphenylmethoxy)methyl]piperidin-4-oneHCID 454896741-Bromo-4-{[(2S)-3-methoxy-2-methylpropoxy]methyl}benzene

Product 1

HCID 66886139HCID 66886139, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.32 mmol of 1,2-dibromoethane are added to a suspension of 156.518 mmol of magnesium in 20 ml of tetrahydrofuran under argon at room temperature. The reaction mixture is warmed until the magnesium starts to react and then 3 ml of a solution of 151.509 mmol of 1-bromo-4-((S)-3-methoxy-2-methyl-propoxymethyl)-benzene in 170 ml of tetrahydrofuran, followed by the rest of the solution, is added while maintaining a gentle reflux. After 2 hours, the reaction mixture is cooled to room temperature and then a solution of 125.214 mmol of 1-benzyl-3-trityloxymethyl -piperidin-4-one [234757-27-8] in 170 ml of tetrahydrofuran is slowly added, taking care to keep the internal reaction temperature under 40° C. After overnight stirring at room temperature, the reaction mixture is quenched with saturated aqueous ammonium chloride solution. Ethyl acetate is added to the reaction mixture and the phases separated—the organic phase is washed successively with water and brine. The combined aqueous phases are back-extracted with ethyl acetate—the combined organic phases are dried with sodium sulfate and evaporated. The residue is purified by flash chromatography (SiO2 60F) to afford the title compound as a yellow oil. Rf=0.30 (EtOAc-heptane-25% ammonia conc. 100:100:1); Rt=5.43 (gradient I).

Workup

  1. customto react
  2. additionis added
  3. temperaturewhile maintaining a gentle reflux
  4. customunder 40° C
  5. customthe reaction mixture is quenched with saturated aqueous ammonium chloride solution
  6. additionEthyl acetate is added to the reaction mixture
  7. washthe phases separated—the organic phase is washed successively with water and brine
  8. extractionThe combined aqueous phases are back-extracted with ethyl acetate—the combined organic phases
  9. dry with materialare dried with sodium sulfate
  10. customevaporated
  11. customThe residue is purified by flash chromatography (SiO2 60F)

Sources & evidence

ORD record
ord-78e686c0ba8541618003aafb513d563d
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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