Lithium Hydroxide → N-Boc-4-cyanopiperidine-4-carboxylic acid

HRID 423062

Reaction equation

HRID 423062 reaction equation
[OH-].[Li+].[C:3]([C:5]1([C:18]([O:20]CC)=[O:19])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)#[N:4]>C1COCC1.C(OCC)C>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([C:3]#[N:4])([C:18]([OH:20])=[O:19])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 577503761-tert-Butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate2×

Product 1

HCID 57750275N-Boc-4-cyanopiperidine-4-carboxylic acidYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

An aqueous solution of lithium hydroxide (2M, 39.0 mL, 77.92 mmol) was added to a stirred solution of 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate (Intermediate 7) (5.5 g, 19.48 mmol), in THF (78 mL) at 25° C. The resulting mixture was stirred at 25° C. for 3 hours and monitored by TLC. The reaction mixture was diluted with diethyl ether (150 mL), and washed with water (100 mL). The aqueous layers were combined and then acidified with citric acid (1N, 200 mL). The product was extracted into DCM. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford 1-(tert-butoxycarbonyl)-4-cyanopiperidine-4-carboxylic acid (4.50 g, 91%). This material was used in the next steps without further purification.

Workup

  1. washwashed with water (100 mL)
  2. extractionThe product was extracted into DCM
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-913c783346914bb1a7ddaff84e3acc07
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Linked notes

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