Tetrahydrofuran → HCID 17608004, compound

HRID 859216Notes

Reaction equation

HRID 859216 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[O:4].[OH-].[Na+].O1CCCC1>O>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]([N:7]3[C:8](=[O:10])[CH2:9][CH:5]([C:3]([OH:4])=[O:2])[CH2:6]3)=[CH:16][CH:15]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68614531HCID 68614531, compound

Product 1

HCID 17608004HCID 17608004, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 7.12 g (20.7 mmol) of (RS)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester in 10.3 ml of a solution of sodium hydroxide (1N) is prepared and tetrahydrofurane is added until a clear solution is obtained. The mixture is heated to 50° C. for 1 hour. For the working-up, the tetrahydrofurane is evaporated under reduced pressure. The white suspension obtained is diluted with water, then filtered. The white product is treated with toluene and evaporated under reduced pressure to remove most of the water. The azetropic distillation is repeated three times. There are obtained 5.78 g (85% of theory) of (RS)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid as a white solid.

Workup

  1. customis prepared
  2. customis obtained
  3. customthe tetrahydrofurane is evaporated under reduced pressure
  4. customThe white suspension obtained
  5. filtrationfiltered
  6. additionThe white product is treated with toluene
  7. customevaporated under reduced pressure
  8. customto remove most of the water
  9. distillationThe azetropic distillation

Sources & evidence

ORD record
ord-e2d23dfd230e430ea84bd6ec1f033808
Source dataset
uspto-grants-2006_12
Patent number
US07151111B2

Reaction notes

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