Tetrahydrofuran → HCID 68310231, compound

HRID 2171635Notes

Reaction equation

HRID 2171635 reaction equation
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[CH:11]=[N:12][C:13]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24]CC)=[O:23])[CH2:18][CH2:17]2)=[N:14][CH:15]=1.C1COCC1.[OH-].[Na+]>CCO>[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[CH:11]=[N:12][C:13]([N:16]2[CH2:17][CH2:18][CH:19]([C:22]([OH:24])=[O:23])[CH2:20][CH2:21]2)=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68309609HCID 68309609, compound

Product 1

HCID 68310231HCID 68310231, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 1-{5-[2-fluoro-3-(hydroxymethyl)phenyl]pyrimidin-2-yl}piperidine-4-carboxylate (1.4 g) was mixed with THF (10 ml) and EtOH (15 ml), and a 1M aqueous NaOH solution (5.8 ml) was added thereto, followed by stirring at room temperature overnight. The insoluble matter was collected by filtration, and the filtrate was concentrated under reduced pressure. Water and 1M hydrochloric acid (5.8 ml) were added to the obtained residue at 0° C., followed by stirring at 0° C. for 30 minutes. The solid was collected by filtration, washed with water, and then dried at 50° C. under reduced pressure to obtain 1-{5-[2-fluoro-3-(hydroxymethyl)phenyl]pyrimidin-2-yl}piperidine-4-carboxylic acid (1.29 g).

Workup

  1. filtrationThe insoluble matter was collected by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater and 1M hydrochloric acid (5.8 ml) were added to the obtained residue at 0° C.
  4. stirringby stirring at 0° C. for 30 minutes
  5. filtrationThe solid was collected by filtration
  6. washwashed with water
  7. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-de3c2f56b8b34a2582ff0ce3403e29e8
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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