Lithium Hydroxide → HCID 20988035, compound

HRID 404650Notes

Reaction equation

HRID 404650 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([O:13]CC)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[NH2:2].[OH-].[Li+]>CCO.O>[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86688908HCID 86688908, compound

Product 1

HCID 20988035HCID 20988035, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(4-carbamoylpiperidin-1-yl)-2-phenylacetate (202 mg, 0.69 mmol) was dissolved in a mixture EtOH (4.6 ml) and water (2.3 ml), and lithium hydroxide (50.0 mg, 2.09 mmol) was added. The reaction was stirred at room temperature overnight. LiOH (33.3 mg, 1.39 mmol) was added in two portions in the following two days. EtOH was evaporated and 1N HCl was added dropwise to the aqueous solution till pH 6-7. The solution was evaporated and the residue was purified by flash chromatography (DCM/MeOH=7/3 to 6/4) to obtain 2-(4-carbamoylpiperidin-1-yl)-2-phenylacetic acid (155 mg, 85% yield) as a white solid.

Workup

  1. additionwas added
  2. customEtOH was evaporated
  3. addition1N HCl was added dropwise to the aqueous solution till pH 6-7
  4. customThe solution was evaporated
  5. customthe residue was purified by flash chromatography (DCM/MeOH=7/3 to 6/4)

Sources & evidence

ORD record
ord-8fc9f023a1734e70ae5e696de31fade0
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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