HCID 57296559, compound → HCID 86331931, compound

HRID 1086800Notes

Reaction equation

HRID 1086800 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[O:2]2>C(O)(=O)C.O.[Zn]>[OH:2][C@@H:1]1[CH2:6][CH2:5][C@H:4]([NH:3][C:8](=[O:9])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1

Participants

5

Reactant 1

HCID 57296559HCID 57296559, compound

Product 1

HCID 86331931HCID 86331931, compoundYield 23.8%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent3×HCID 962WaterSolvent

Procedure

A solution 3-aza-2-oxabicyclo[2.2.1]heptane-3-carboxylic acid, (phenylmethyl) ester (0.5 g) in glacial acetic acid (0.5 ml) was added to a stirred suspension of powdered zinc (0.35 g) in a mixture of acetic acid and water (1:1; 4 ml), and the mixture was stirred at 60° for 7.5 h. Additional zinc powder (0.14 g) and acetic acid (1 ml) were added and stirring was continued for a further 16.5 h. After cooling to room temperature, the mixture was filtered and the excess of zinc washed with 2M hydrochloric acid (20 ml). The combined filtrate and washings were neutralised with 8% sodium carbonate and extracted into ethyl acetate (3×30 ml). The combined organic extracts were washed with brine (30 ml), dried and concentrated in vacuo. Purification by FCC eluting with ethyl acetate: cyclohexane (1:1) gave an oil (120 mg) which solidified upon standing and was recrystallised from cyclohexane to give the title compound (70 mg), m.p. 62°-63°.

Workup

  1. stirringstirring
  2. waitwas continued for a further 16.5 h
  3. filtrationthe mixture was filtered
  4. washthe excess of zinc washed with 2M hydrochloric acid (20 ml)
  5. extractionextracted into ethyl acetate (3×30 ml)
  6. washThe combined organic extracts were washed with brine (30 ml)
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customPurification by FCC
  10. washeluting with ethyl acetate: cyclohexane (1:1)

Sources & evidence

ORD record
ord-6e2643c00103427dace5973aeb37e87a
Source dataset
uspto-grants-1991_07
Patent number
US05032583

Reaction notes

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