Sodium Hydroxide → HCID 45074199, compound

HRID 2360964Notes

Reaction equation

HRID 2360964 reaction equation
C[O:2][C:3]([C:5]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[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)=[O:4].[OH-].[Na+]>C1COCC1.CO>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:23][CH:24]=2)([C:3]([OH:4])=[O:2])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67385182HCID 67385182, compound

Product 1

HCID 45074199HCID 45074199, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-biphenyl-4-ylmethyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (11.4 mmol; 4.65 g) in THF (30 mL) and methanol (20 mL) was added a 1M solution of sodium hydroxide (28.4 mmol; 28.4 mL) and the resulting mixture was heated to reflux for 48 hours. The resulting mixture was then evaporated and a 1N hydrochloric acid solution (200 mL) was added to the residue. A white precipitate formed that was separated via filtration to yield 4-biphenyl-4-ylmethyl-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester. MS (ESI) m/z 395.76 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 48 hours
  3. customThe resulting mixture was then evaporated
  4. additiona 1N hydrochloric acid solution (200 mL) was added to the residue
  5. customA white precipitate formed
  6. customthat was separated via filtration

Sources & evidence

ORD record
ord-ea9cf937084b4cfc93104236cee09365
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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