Benzyl Bromide → 4-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

HRID 1611733Notes

Reaction equation

HRID 1611733 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH2:23]([O:15][C:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)=[O:16])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 222559134-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylateYield 104.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-tert-butoxycarbonyl-piperidine-4-carboxylic acid (20 g) in DMF (100 ml) was treated with anhydrous potassium carbonate (60 g) and then benzyl bromide (16.43 g) and the mixture was stirred at room temperature for 72 hours. It was filtered, evaporated to dryness, dissolved in ethyl acetate, washed with sodium carbonate solution and water and dried over sodium sulfate. The product was evaporated to give an oil (29 g).

Workup

  1. filtrationIt was filtered
  2. customevaporated to dryness
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with sodium carbonate solution and water
  5. dry with materialdried over sodium sulfate
  6. customThe product was evaporated

Sources & evidence

ORD record
ord-2160915f63a74c17a07eb2965f8c71a2
Source dataset
uspto-grants-2006_01
Patent number
US06989447B2

Reaction notes

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