Hydrochloric Acid → 1-[(Tert-butoxy)carbonyl]-4-ethylpiperidine-4-carboxylic acid

HRID 2179755Notes

Reaction equation

HRID 2179755 reaction equation
[CH2:1]([C:3]1([C:16]([O:18]CC)=[O:17])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)[CH3:2].[OH-].[K+].Cl>C(O)C.O>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C:3]([CH2:1][CH3:2])([C:16]([OH:18])=[O:17])[CH2:4][CH2:5]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 53393415Ethyl 1-Boc-4-ethyl-4-piperidine carboxylate

Product 1

HCID 221690971-[(Tert-butoxy)carbonyl]-4-ethylpiperidine-4-carboxylic acidYield 90.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 1-tert-butyl 4-ethyl 4-ethylpiperidine-1,4-dicarboxylate (Intermediate 21-step 2, 10.0 g, 63.69. mmol) in 50 ml ethanol was added potassium hydroxide (8.0 g, 95.5 mmol) and the contents were refluxed for 16 hours. Upon completion of the reaction (monitored by TLC), the reaction mixture was diluted with water, acidified with 5% HCl and extracted with DCM. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (8.2 g) as a light yellow liquid. 1H NMR (300 MHz, CDCl3): 1.44 (s, 9H); 2.07-2.11 (m, 2H); 2.28 (s, 1H); 2.82 (s, 2H); 2.92-2.95 (m, 1H); 3.46-3.52 (m, 3H); ES Mass: 280 (100%), [M+Na].

Workup

  1. temperaturethe contents were refluxed for 16 hours
  2. customUpon completion of the reaction (monitored by TLC)
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-99880fcfb1374713930cc54d7561acdd
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

Loading…