Water → HCID 66609159, compound

HRID 1529571Notes

Reaction equation

HRID 1529571 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](=O)[CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13](=[O:28])[CH2:12]1)=[O:10])[CH3:7].O>O1CCOCC1>[CH2:6]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2[N:17]=[C:18]([CH2:19][O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:28][C:13]=2[CH2:12]1)=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 66609320HCID 66609320, compound

Product 1

HCID 66609159HCID 66609159, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (9.3 mL, 99.9 mmol) was added to a stirred solution of 3-oxo-4-(2-phenoxy-acetylamino)-piperidine-1-carboxylic acid ethyl ester (30.3 g, 90.8 mmol) in 1,4-dioxane (454 mL). The mixture was stirred at 100° C. for 2 hours. The mixture was cooled at 0° C., treated with water and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The product was purified by flash column chromatography (AcOEt in DCM 0/100 to 30/70). The desired fractions were collected and evaporated in vacuo to yield 2-phenoxymethyl-6,7-dihydro-4H-oxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (23.2 g, 84% yield) as a colourless oil.

Workup

  1. temperatureThe mixture was cooled at 0° C.
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo
  7. customThe product was purified by flash column chromatography (AcOEt in DCM 0/100 to 30/70)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-9c4fcfd3541d44b481a977483dd434d0
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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