Methanol → 1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

HRID 711378Notes

Reaction equation

HRID 711378 reaction equation
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][CH:4]([C:7]([O:9]C)=[O:8])[CH2:3][CH2:2]1.[Li+].[OH-].CO.O>C1COCC1>[C:14]([O:13][C:11]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl ester

Product 1

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-tert-butyl 4-methyl piperidine-1,4-dicarboxylate (4.84 g 20 mmol), and LiOH (2.52 g, 60 mmol) in THF (90 mL)/MeOH (90 mL)/H2O (30 mL) was stirred at r.t overnight. Then the solvents were removed, and the pH of the residue was adjusted to 2 by using 2N HCl. The resulting mixture was extracted with EtOAc (3×20 mL). The combined organic layers were dried over Na2SO4, and concentrated to give 1-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (4.6 g, yield 100.0%).

Workup

  1. customThen the solvents were removed
  2. extractionThe resulting mixture was extracted with EtOAc (3×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-da6a56c03eb1456684e0c7faef2b4dae
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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