Ammonium Acetate → Piperidine-3,3-dicarboxylic acid 3-benzyl 3-(3,3-dimethyl-2-oxobutyl) ester

HRID 2407498Notes

Reaction equation

HRID 2407498 reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[C:3](=[O:32])[CH2:4][O:5][C:6]([C:8]1([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:13][CH2:12][CH2:11][N:10](C(OCC(Cl)(Cl)Cl)=O)[CH2:9]1)=[O:7].C([O-])(=O)C.[NH4+]>O1CCCC1.[Zn]>[CH3:1][C:2]([CH3:34])([CH3:33])[C:3](=[O:32])[CH2:4][O:5][C:6]([C:8]1([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:13][CH2:12][CH2:11][NH:10][CH2:9]1)=[O:7]

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 67544698Piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3-benzyl 3-(3,3-dimethyl-2-oxobutyl)ester

Product 1

HCID 67544909Piperidine-3,3-dicarboxylic acid 3-benzyl 3-(3,3-dimethyl-2-oxobutyl) ester

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of piperidine-1,3,3-tricarboxylic acid 1-(2,2,2-trichloroethyl) 3-benzyl 3-(3,3-dimethyl-2-oxobutyl)ester (1.6 g 3 mmol) and zinc (10.5 g 0.16 mol) in a mixture of tetrahydrofurane (25 mL) and 1M aqueous solution of ammonium acetate (13 mL) is stirred overnight at room temperature, diluted with tetrahydrofurane (20 mL) and filtrated over clarcel. The filtrate is diluted with dichloromethane, washed with water dried over magnesium sulfate and concentrated under reduced pressure to give piperidine-3,3-dicarboxylic acid 3-benzyl 3-(3,3-dimethyl-2-oxobutyl)ester as an oil

Workup

  1. filtrationfiltrated over clarcel
  2. additionThe filtrate is diluted with dichloromethane
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1f41bc4b4bc74599a59876ef4eea17d8
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

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