Acetic Acid → HCID 67544807, compound

HRID 2407490Notes

Reaction equation

HRID 2407490 reaction equation
[CH2:1]([O:8][C:9]([C:11]1([C:24]([O:26]CC2C=CC=CC=2)=[O:25])[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K].C(O)(=O)C>CN(C)C=O.O>[CH2:1]([O:8][C:9]([C:11]1([C:24]([OH:26])=[O:25])[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5462222PotassiumHCID 67544413HCID 67544413, compound

Product 1

HCID 67544807HCID 67544807, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of piperidine-1,3,3-tricarboxylic acid 1-tert-butyl 3,3-dibenzyl ester (3.59 g 7.9 mmol) in N,N-dimethylformamide (100 mL) cooled with a water/ice bath, is added dropwise a solution of potassium hydroxyde (0.68 g 85% 10 mmol) in water (29 mL). The mixture is further stirred with cooling for 2 h, then allowed to warm to room temperature and acidified with acetic acid (1.05 eq). After concentration under reduced pressure, the crude product is dissolved in diisopropyl oxyde, washed with water, dried over magnesium sulphate and concentrated under reduced pressure to give piperidine-1,3,3-tricarboxylic acid 1-tert-butyl 3-benzyl ester as an oil.

Workup

  1. temperaturewith cooling for 2 h
  2. concentrationAfter concentration under reduced pressure
  3. dissolutionthe crude product is dissolved in diisopropyl oxyde
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2d730c19aa8448efa738cd407ad77d9e
Source dataset
uspto-grants-2014_08
Patent number
US08809539B2

Reaction notes

Loading…