3-Chlorobenzoic Acid → tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylate

HRID 1360171Notes

Reaction equation

HRID 1360171 reaction equation
[OH:1][C:2]1[CH2:3][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5](O)=[CH:6][CH:7]=1.ClC1C=C(C=CC=1)C(O)=O.C(OC(=O)C)C>C(Cl)Cl>[CH:2]12[O:1][CH:7]1[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]2

Participants

5

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 8857Ethyl AcetateHCID 66969636HCID 66969636, compound2×

Product 1

HCID 21991116tert-Butyl 7-Oxa-3-azabicyclo(4.1.0)heptane-3-carboxylateYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.1 g (11.5 mmol) of t-butyl 3,6-dihydroxypyridin-1(2H)-carboxylate (product of step 1) and 3.1 g (12.6 mmol) of m-chloro benzoic acid was dissolved in 30 mL of methylene chloride, and after stirring for 5 hour, 100 mL of ethylacetate was added thereto. After washing with water, an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography to give 2.1 g (10.5 mmol) of the title compound in a yield of 87%.

Workup

  1. washAfter washing with water
  2. dry with materialan organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1d219916e0f0452e95527e9039895246
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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