Water → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 1808354Notes

Reaction equation

HRID 1808354 reaction equation
O.C(=O)(O)[O-].[Na+].[NH:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1.[C:16](Cl)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1>[CH2:19]([O:18][C:16]([N:7]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Water (75 ml), followed by sodium bicarbonate (30.8 g), was added to piperidine-4-carboxylic acid (25 g) in THF (75 ml). The mixture was cooled to 0° C., and Cbz chloride (38.9 ml) was added dropwise. The reaction mixture was then stirred for 5 h at room temperature (TLC monitoring). When the conversion was complete, the organic solvent was distilled off and the residue was taken up in water (200 ml) and washed with ethyl acetate (2×150 ml). The aqueous phase was acidified with dilute aqueous HCl solution and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo. Yield: 48.5 g (96%)

Workup

  1. distillationthe organic solvent was distilled off
  2. washwashed with ethyl acetate (2×150 ml)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbe20b5052664c1c9c931fd9258f034f
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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