Sodium Bicarbonate → cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

HRID 600720Notes

Reaction equation

HRID 600720 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=1.[C:13]([N:20]1[CH2:24][CH2:23][CH:22]=[CH:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:16]([O:15][C:13]([N:20]1[CH2:24][C@H:23]2[C@H:22]([C:3]([C:4]3[CH:5]=[N:6][C:7]([O:10][CH3:11])=[CH:8][CH:9]=3)=[N:2][O:1]2)[CH2:21]1)=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10844857tert-Butyl 2,3-dihydro-1H-pyrrole-1-carboxylateHCID 76564447N-Hydroxy-6-methoxy-3-pyridinecarboximidoyl chloride

Product 1

HCID 68971835cis-3-(6-Methoxypyridin-3-yl) 3a,4,6,6a-tetrahydro-pyrrolo[3,4-d]isoxazole-5-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Chloro oxime 2c (1.12 g; 5.99 mmol), N-Boc-pyrroline (0.5 mL; 2.90 mmol) and sodium bicarbonate (0.61 g) in ethyl acetate (40 mL) were stirred at room temperature for 24 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4), filtered and evaporated to yield crude cycloadduct. 3c was isolated as a white solid after chromatography with 25% ethyl acetate/hexanes.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto yield crude cycloadduct

Sources & evidence

ORD record
ord-2f035dffe65f4a80ae0715be7fe1d85d
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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