Water → HCID 67547958, compound

HRID 1880218Notes

Reaction equation

HRID 1880218 reaction equation
C([O:3][C:4]([CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[CH2:9][N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:18]([N:8]1[CH2:9][CH:10]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[CH:6]([CH2:4][OH:3])[CH2:7]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12922293Ethyl 1-benzyl-4-(4-fluorophenyl)pyrrolidine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 67547958HCID 67547958, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3SR,4RS) 1-Benzyl-4-(4-fluoro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (CAS RN: 874990-58-6) (20 g, 0.061 mol) were dissolved in THF (600 mL). At 0° C. LiAlH4 (2.8 g, 0.073 mol) was added portion wise. After stirring at 0° C. for 4 h water (15 mL), then 5N NaOH (15 mL) and additional water (25 mL) was added. After stirring at ambient temperature for 1 h the mixture was extracted with ethyl acetate (3×50 mL), the combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude title product was obtained as a light yellow oil (14.95 g, 86%) and directly used in the next step.

Workup

  1. customAt 0° C
  2. extractionwas extracted with ethyl acetate (3×50 mL)
  3. customthe combined organic phases were dried on sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-033b58296de3442a861c11b67d39f9ef
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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