Water → HCID 18423463, compound

HRID 1281994Notes

Reaction equation

HRID 1281994 reaction equation
C([N:4]1[CH2:8][CH:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:6]([C:14](OC)=[O:15])[CH2:5]1)C=C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[OH:15][CH2:14][CH:6]1[CH:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH2:8][NH:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70114387HCID 70114387, compound

Product 1

HCID 18423463HCID 18423463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.1 g (24.5 mmol) of 1-allyl-3-(SR)-carbomethoxy-4-(RS)-(3-thienyl)pyrrolidine in 50 mL of TMF at 0° C. was added 49 mL (49 mmol) of a 1 M solution of lithium aluminum hydride in THF and the reaction was stirred at rt for 12 h. To the reaction mixture was then added 5 mL of water and 5 mL of 2N NaOH. The reaction mixture was extracted with ethyl acetate and the combined organic fractions were washed with sat'd NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated to give the title compound which was used without further purification. Mass spectrum (ESI) m/e=274 (M+1).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe combined organic fractions were washed with sat'd NaCl solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-de37f47b4fb04fc68f1a0763549d39c5
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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