Water → HCID 67464474, compound

HRID 553973Notes

Reaction equation

HRID 553973 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[C:9]=1[C@H:16]1[NH:20][C@@H:19]([C:21](OCC)=[O:22])[CH2:18][CH2:17]1.O.[OH-].[Na+]>C1COCC1>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[C:9]=1[C@H:16]1[NH:20][C@@H:19]([CH2:21][OH:22])[CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67460180HCID 67460180, compound

Product 1

HCID 67464474HCID 67464474, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

LAH (724 mg) was added to a solution of ethyl (2R,5S)-5-(2,4,6-trifluorophenyl)pyrrolidine-2-carboxylate (4.34 g) in THF (100 mL) at −15° C. over one hour. The reaction solution was stirred at −15° C. for 19 hours. Water (0.8 mL), a 5 N sodium hydroxide solution (0.8 mL), and water (2.5 mL) were sequentially added to the reaction solution, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure to obtain 3.68 g of the title compound. The property values of the compound are as follows.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. filtrationThe reaction solution was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-49316d30ff7344739b401caffcdba14b
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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