Phenylacetaldehyde → HCID 69037927, compound

HRID 2113059Notes

Reaction equation

HRID 2113059 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[C:17](=[O:31])[N:18]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:19]([CH3:22])=[CH:20][CH:21]=1.[C:32]1([CH2:38][CH:39]=O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(O)(=O)C.ClCCCl>[CH3:22][C:19]1[N:18]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17](=[O:31])[C:16]([NH:15][CH2:39][CH2:38][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 998PhenylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 104901153-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

Product 1

HCID 69037927HCID 69037927, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolvent

Procedure

Sodium triacetoxyborohydride (0.67 g, 3.15 mmol) was added to a stirred solution of tert-butyl 2-[3-amino-6-methyl-2-oxo-1(2H)-pyridinyl]acetate (EXAMPLE 1, STEP 1-3), (0.5 g, 2.10 mmol) and phenyl acetaldehyde (0.18 mL, 2.33 mmol) in 0.24 M acetic acid (0.14 mL) in 1,2-dichloroethane (11 mL). After 16 h the mixture was quenched with water and extracted into ethylacetate. The ethyl acetate layer was washed with sodium carbonate solution and brine, dried (Na2SO4) and evaporated under reduced pressure to a glass. The crude product was purified by flash column chromatography (silicagel, eluant CH2Cl2/MeOH=40/1) to give 0.34 g (1.00 mmol) of a light blue solid compound.

Workup

  1. customAfter 16 h the mixture was quenched with water
  2. extractionextracted into ethylacetate
  3. washThe ethyl acetate layer was washed with sodium carbonate solution and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure to a glass
  6. customThe crude product was purified by flash column chromatography (silicagel, eluant CH2Cl2/MeOH=40/1)

Sources & evidence

ORD record
ord-509102f158b74e2e82e6bc5a41b4f254
Source dataset
uspto-grants-2009_04
Patent number
US07524871B2

Reaction notes

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