Hydrochloric Acid → HCID 19439052, compound

HRID 1920751Notes

Reaction equation

HRID 1920751 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:18])[CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:10][CH2:9]1)C.Cl>O.C(O)C>[C:14]([N:11]1[CH2:10][CH2:9][CH:8]([CH2:7][C:6]([OH:18])=[O:5])[CH2:13][CH2:12]1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57733330HCID 57733330, compound

Product 1

HCID 19439052HCID 19439052, compoundYield 19.7%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a solution of NaOH in water/ethanol (v/v=40/10, 50 mL) (1-tert-butyl-piperidin-4-yl)-acetic acid ethyl ester (4.03 g, 17.8 mmol) was added and the mixture was stirred at r.t. overnight. 1 N aq. HCl was added to adjust the pH to 5. Volotiles were evaporated in vacuo, the residue was diluted with methanol (30 mL), and the insoluble inorganic salts were removed by filtration. The filtrate was concentrated and purified by column chromatography on silica gel (CH2Cl2/MeOH=20/1 to 5/1) to give 0.7 g of title compound as a light grey powder. 1H NMR (400 MHz, DMSO-d6): 3.15-3.08 (br m, 2H), 2.30 (br t, J=11.2 Hz, 2H), 2.05 (d, J=6.4 Hz, 2H), 1.71-1.68 (m, 3H), 1.30-1.27 (m, 2H), 1.10 (s, 9H).

Workup

  1. customVolotiles were evaporated in vacuo
  2. additionthe residue was diluted with methanol (30 mL)
  3. customthe insoluble inorganic salts were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography on silica gel (CH2Cl2/MeOH=20/1 to 5/1)

Sources & evidence

ORD record
ord-40771122922846a89c7a0486c0cb24c2
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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