Benzyl Bromide → HCID 66687435, compound

HRID 1895009Notes

Reaction equation

HRID 1895009 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:20][CH2:19][CH:18]([C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[C:9]([O:13][C:14]([N:16]1[CH2:20][CH2:19][C:18]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 66687908HCID 66687908, compound

Product 1

HCID 66687435HCID 66687435, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl bromide (0.19 mL, 1.60 mmol) was added to a solution of 3-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (138 mg, 0.40 mmol) in THF (5 mL), and then lithium bis(trimethylsilyl)amide (1.0 M, in THF, 1.2 mL, 1.20 mmol) was slowly added at room temperature. The reaction mixture was stirred at room temperature for 1.5 hours, then was quenched by addition of saturated aqueous NH4Cl, diluted with water, and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (10% to 20% of EtOAc in hexane) to give 40 mg (23% yield) of 3-benzyl-3-(3,4-dichloro-benzoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a colorless oil.

Workup

  1. customwas quenched by addition of saturated aqueous NH4Cl
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (10% to 20% of EtOAc in hexane)

Sources & evidence

ORD record
ord-8a6650e36f0d4de4a39bd14101305645
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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