Hydrochloric Acid → 1-((Tert-butoxy)carbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 655946Notes

Reaction equation

HRID 655946 reaction equation
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][CH2:5][C:4]([C:11]([O:13]C)=[O:12])([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[Li+].[OH-].Cl>C1COCC1.CO>[C:18]([O:17][C:15]([N:1]1[CH2:2][CH2:3][C:4]([C:7]([O:9][CH3:10])=[O:8])([C:11]([OH:13])=[O:12])[CH2:5][CH2:6]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 579202841-Tert-butyl 4,4-dimethyl piperidine-1,4,4-tricarboxylate

Product 1

HCID 579202821-((Tert-butoxy)carbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-tert-butyl 4,4-dimethyl piperidine-1,4,4-tricarboxylate (6.2 g, 20.5 mmol) in THF (11 mL) and CH3OH (11 mL) was added aqueous LiOH (2 N, 11 mL, 22 mmol, 1.1 equiv.). The reaction mixture was stirred at 80° C. for 1 h. The reaction mixture was neutralized with HCl (1N) and was concentrated to dryness. The residue was dissolved in ethyl acetate and dried over Na2SO4 and concentrated to give 1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid (4.7 g, 80%), which was used without further purification. LRMS (M+H+-Boc) m/z 188.0.

Workup

  1. concentrationwas concentrated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0eb8ca6bc06144f494b88536b05791b2
Source dataset
uspto-grants-2011_12
Patent number
US08071625B2

Reaction notes

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