Ethyl 1-benzyl-4-(trifluoromethyl)pyrrolidine-3-carboxylate → [1-Benzyl-4-(trifluoromethyl)pyrrolidin-3-yl]methanol

HRID 2296831Notes

Reaction equation

HRID 2296831 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]([F:16])([F:15])[F:14])[CH:10]([C:17](OCC)=[O:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]([F:16])([F:14])[F:15])[CH:10]([CH2:17][OH:18])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 18388374Ethyl 1-benzyl-4-(trifluoromethyl)pyrrolidine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 18388364[1-Benzyl-4-(trifluoromethyl)pyrrolidin-3-yl]methanolYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.8 g (6 mmol) of 1-benzyl-3-(RS)-carboethoxy-4-(RS)-trifluoromethylpyrrolidine in 20 mL of THF at 0° C. was added 4.8 mL (4.8 mmol) of a 1M solution of LAH in THF and the reaction was stirred at rt for 30 min. The reaction mixture was quenched with 5N NaOH solution and extracted with ether. The combined organic fractions were washed with 2N NaOH solution and sat'd NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:8) to give 1.5 g of the title compound.

Workup

  1. customThe reaction mixture was quenched with 5N NaOH solution
  2. extractionextracted with ether
  3. washThe combined organic fractions were washed with 2N NaOH solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by chromatography (silica, acetone:hexanes, 1:8)

Sources & evidence

ORD record
ord-87373558623c42c59dfb13dc83b3360f
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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