Butanal → HCID 59717705, compound

HRID 2224644Notes

Reaction equation

HRID 2224644 reaction equation
C(N(CC)CC)C.[CH:8](=O)[CH2:9][CH2:10][CH3:11].[F:13][C:14]([F:24])([F:23])[C:15]([N:17]1[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18]1)=[O:16].[H][H]>C(O)C.[Pd]>[CH2:8]([NH:22][C@H:19]1[CH2:20][CH2:21][N:17]([C:15](=[O:16])[C:14]([F:13])([F:23])[F:24])[CH2:18]1)[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 261ButanalHCID 8471TriethylamineHCID 10845131HCID 10845131, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59717705HCID 59717705, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Triethylamine (1.9 mL, 13.72 mmol) and butanal (1.3 mL, 14.41 mmol) were added to a solution of (S)-1-(trifluoroacetyl)pyrrolidin-3-yl amine (3.0 g, 13.72 mmol) (J. Med. Chem., 1996, 39(14), pg. 2771, No. 6) in ethanol (60 mL). The reaction mixture was treated with 10% Pd/C (300 mg) and placed under about 415 kPa (about 60 psi) of hydrogen at room temperature for 18 hours. The reaction mixture was filtered through Arbocel®, washing through with ethyl acetate. The filtrate was washed with saturated sodium hydrogencarbonate solution, dried over magnesium sulphate and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with ethyl acetate:pentane:triethylamine 25:75:0 to 100:0:0 to 99:0:1 to yield the title product.

Workup

  1. filtrationThe reaction mixture was filtered through Arbocel®
  2. washwashing through with ethyl acetate
  3. washThe filtrate was washed with saturated sodium hydrogencarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel eluting with ethyl acetate:pentane:triethylamine 25:75:0 to 100:0:0 to 99:0:1

Sources & evidence

ORD record
ord-437f5ae62c5e41758c89b630bdb9868e
Source dataset
uspto-grants-2008_05
Patent number
US07378436B2

Reaction notes

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