Water → HCID 118415299, compound

HRID 1775776Notes

Reaction equation

HRID 1775776 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]([CH3:24])[C@@H:15]([CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[C:16](O)=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([N:14]([CH3:24])[C@@H:15]([CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:16][OH:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 118415278HCID 118415278, compound

Product 1

HCID 118415299HCID 118415299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (2.3 g, 61.0 mmol, 1.5 eq) in anhydrous THF (200 mL) at 0° C. was added (S)-2-(benzyl(methyl)amino)-2-cyclopentylacetic acid (3) (10.0 g, 40.0 mmol, 1.0 eq) in portions at 0° C. The reaction mixture was stirred at room temperature for 2 h followed by heating to reflux for 2 h, After cooled, water (2.5 mL) was added at 0° C. followed by 5% NaOH (2.5 mL, aq). The suspension formed was filtered and washed with ethyl acetate (50 mL). Water (250 mL) was then added to the filtrate, which was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulphate and evaporated in vacuo to give the product 4 as an oil (quant); LC-MS: m/z 234 [M+H+]+

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 h
  3. temperatureAfter cooled
  4. customThe suspension formed
  5. filtrationwas filtered
  6. washwashed with ethyl acetate (50 mL)
  7. additionWater (250 mL) was then added to the filtrate, which
  8. extractionwas extracted with ethyl acetate
  9. washThe organic layer was washed with brine
  10. dry with materialdried over sodium sulphate
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-5f1e689bd5c744f9953470ee9f9a4df8
Source dataset
uspto-grants-2016_02
Patent number
US09260478B2

Reaction notes

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