Hydrochloric Acid → (3S)-6-Oxopiperidine-3-carboxylic acid

HRID 58878Notes

Reaction equation

HRID 58878 reaction equation
Cl.C(OC([N:9]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:11]([C:16]([OH:18])=[O:17])[CH2:10]1)=O)(C)(C)C>O1CCOCC1>[O:15]=[C:14]1[NH:9][CH2:10][C@@H:11]([C:16]([OH:18])=[O:17])[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 117690989(S)-1-(tert-butoxycarbonyl)-6-oxopiperidine-3-carboxylic acid

Product 1

HCID 42546124(3S)-6-Oxopiperidine-3-carboxylic acidYield 144.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of HCl in dioxane (6M, 10 mL) was added to a solution of (S)-1-(tert-butoxycarbonyl)-6-oxopiperidine-3-carboxylic acid (700 mg, 2.90 mmol) in dioxane (5 mL) at 0° C. with stirring. The reaction mixture was stirred for 4 h and concentrated to dryness. The residue was azeotroped three times with MeOH (10 mL for each portion) to afford (S)-6-oxopiperidine-3-carboxylic acid (600 mg, quantitative) as a colorless solid. (R)-6-oxopiperidine-3-carboxylic acid was made in similar manner.

Workup

  1. stirringThe reaction mixture was stirred for 4 h
  2. concentrationconcentrated to dryness
  3. customThe residue was azeotroped three times with MeOH (10 mL for each portion)

Sources & evidence

ORD record
ord-f5d4099b72764b3bbe20302a32bbf4a1
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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