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

HRID 1921254Notes

Reaction equation

HRID 1921254 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-65029a566e314dd997d562867f945ad9
Source dataset
uspto-grants-2012_05
Patent number
US08173683B2

Reaction notes

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