Sodium Hydroxide → HCID 90015970, compound

HRID 1057051Notes

Reaction equation

HRID 1057051 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2([C:21]([O:23]CC)=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+]>C(O)C>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)([C:21]([OH:23])=[O:22])[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90024521HCID 90024521, compound

Product 1

HCID 90015970HCID 90015970, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of the compound 1-tert-butyl 4-ethyl 4-(2-chloropyridin-4-yl)piperidine-1,4-dicarboxylate (50 g, 0.14 mols, 1 equiv.) in ethanol (75 mL) was added 500 mL of a 10% solution of NaOH. The mixture was refluxed for 2 h. The reaction was monitored by TLC (ethyl acetate/petroleum ether; 1/5), cooled, concentrated to a half of the primary volume and extracted with methyltertiarybutyl ether (3×150 mL). The aqueous layer was acidified with 3M hydrochloric acid to pH=4 and extracted with dichloromethane (2×350 mL). The combined organic layers were dried over anhydrous sodium sulfate. The organic was concentrated to give crude product 1-(tert-butoxycarbonyl)-4-(2-chloropyridin-4-yl)piperidine-4-carboxylic acid (42 g, 91% crude). The crude was used as is in Step C.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. temperaturecooled
  3. concentrationconcentrated to a half of the primary volume
  4. extractionextracted with methyltertiarybutyl ether (3×150 mL)
  5. extractionextracted with dichloromethane (2×350 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  7. concentrationThe organic was concentrated

Sources & evidence

ORD record
ord-b31845cc3d614d39b8437e3d83226324
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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