Tetrahydrofuran → HCID 68310231, compound

HRID 1021235Notes

Reaction equation

HRID 1021235 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 1 M 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 1 M 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 1 M 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-940a11dbad3d4577bf649eee372b19e8
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

Loading…