Water → HCID 23036274, compound

HRID 1709863Notes

Reaction equation

HRID 1709863 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:18][N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:16](=O)[C:15]2(C2C=CC(F)=CC=2)[CH2:27]O)=[CH:10][CH:9]=1.[OH2:36].[OH-].[Na+]>O1CCCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=2)([CH:15]2[CH2:27][CH2:18][N:17]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:16]2)[OH:36])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 86744171HCID 86744171, compound

Product 1

HCID 23036274HCID 23036274, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slurry of 7.6 g (0.02 mole) of lithium aluminum hydride in 150 ml of freshly distilled tetrahydrofuran was added dropwise, over a 45 min period, a solution of 38.5 g (0.098 mole) of 4-[bis(4-fluorophenyl)hydroxymethyl-1-(phenylmethyl)-2-pyrrolidinone in 150 ml of tetrahydrofuran. After the addition was complete, the mixture was heated at reflux for 2 hr and then let stir at ambient temperature overnight. The excess lithium aluminum hydride was decomposed by the successive addition of 8 ml of water, 8 ml of a 15% sodium hydroxide solution, and 24 ml of water. The mixture was stirred for 30 min and filtered. The filtrate was concentrated under reduced pressure and the residue crystallized when triturated with petroleum ether (30°-60° C.). The solid was collected by filtration and recrystallized from 2-propanol to yield 30.3 g (81%) of the title compound as a white solid, mp 99°-100° C.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 hr
  4. stirringThe mixture was stirred for 30 min
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue crystallized when
  8. customtriturated with petroleum ether (30°-60° C.)
  9. filtrationThe solid was collected by filtration
  10. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-254e691824e14dc69cd53b4d93a86f3e
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

Loading…