4-Pyridinecarboxaldehyde → Trans-(4,5-dihydro-5-(pyridin-4-yl)oxazol-4-yl)(pyrrolidin-1-yl)methanone

HRID 75715Notes

Reaction equation

HRID 75715 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[OH-].[K+].[N+:11]([CH2:13][C:14]([N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15])#[C-:12]>CO>[N:1]1[CH:6]=[CH:5][C:4]([C@@H:7]2[O:8][CH:12]=[N:11][C@H:13]2[C:14]([N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 14797Potassium HydroxideHCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-

Product 1

HCID 66901538Trans-(4,5-dihydro-5-(pyridin-4-yl)oxazol-4-yl)(pyrrolidin-1-yl)methanoneYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 19 was prepared in accordance with method B using pyridine-4-carbaldehyde (1.88 mL, 19.76 mmol), KOH (1.01 g, 18.00 mmol) in methanol (18 mL) and 2-isocyano-1-(pyrrolidin-1-yl)ethanone BLE 04098 (2.73 g, 19.76 mmol). The residue was partitioned between ethyl acetate (200 mL) and water (150 mL). The organic layer was combined with additional ethyl acetate extracts (2×150 mL), washed with aqueous sodium chloride (2×150 mL) and dried over MgSO4, filtered and evaporated. Trans-(4,5-dihydro-5-(pyridin-4-yl)oxazol-4-yl)(pyrrolidin-1-yl)methanone Compound 19 was obtained as a white solid (4.32 g, 98% yield).

Workup

  1. customCompound 19 was prepared in accordance with method B
  2. customThe residue was partitioned between ethyl acetate (200 mL) and water (150 mL)
  3. washwashed with aqueous sodium chloride (2×150 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d8e957a5ffe24beeb2bee4c3963eb2ef
Source dataset
uspto-grants-2014_09
Patent number
US08835463B2

Reaction notes

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