Acetic Acid → HCID 86697913, compound

HRID 338099Notes

Reaction equation

HRID 338099 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]12[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH:12]1[CH2:11][O:10][NH:9]2.C(O)(=O)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O.[Zn]>[NH2:9][C:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH:12]([CH2:11][OH:10])[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium Bicarbonate2×HCID 86697914HCID 86697914, compound

Product 1

HCID 86697913HCID 86697913, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 6a-(2-fluorophenyl)-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (5 g, 16.2 mmol) and zinc dust (10.6 g 0.16 mol) is treated with acetic acid (65 mL) in one portion under nitrogen at room temperature. The resulting mixture is stirred for 0.5 hour, diluted with ethyl acetate, and filtered through diatomaceous earth. The filtrate is added drop-wise to a mixture of saturated sodium bicarbonate in water containing an excess of solid sodium bicarbonate (84 g, 1 mol). The mixture is extracted with ethyl acetate, the organic phase is dried over magnesium sulfate, and the solvent removed under vacuum. The residue is purified by silica gel chromatography eluting with ethyl acetate to give the title compound (4.4 g, 87%). ES/MS (m/e): 311(M+H).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. additionThe filtrate is added drop-wise
  3. extractionThe mixture is extracted with ethyl acetate
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. customthe solvent removed under vacuum
  6. customThe residue is purified by silica gel chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-be1cd0d87bb045f6877b76fa0b8a375d
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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