Hydrochloric Acid → HCID 86621492, compound

HRID 61494Notes

Reaction equation

HRID 61494 reaction equation
[O:1]=[C:2]1[C@H:8]2[CH2:9][C@H:4]([CH2:5][CH2:6][C@@H:7]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:3]1.[CH3:17][O-:18].[Na+].Cl>CO>[OH:3][C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@@H:8]([C:2]([O:18][CH3:17])=[O:1])[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 57562755HCID 57562755, compound

Product 1

HCID 86621492HCID 86621492, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

tert-butyl(1S,2S,5S)-7-oxo-6-oxabicyclo[3.2.1]octane-2-carboxylate (5.65 g, 25.0 mmol) was suspended in methanol (20 mL). To that suspension was added a 25 wt % solution of sodium methoxide in methanol (52 mL) and the reaction mixture was stirred at rt for 2 h. Then it was cooled into an ice-water bath and neutralized with a 4 M HCl solution to pH 6. After removing the volatiles, brine was added (50 mL) and the solution was extracted with ethyl acetate (3×40 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to provide the desired product (5.70 g, 88.4% yield). LCMS: m/z 281.1 (M+Na)+.

Workup

  1. temperatureThen it was cooled into an ice-water bath
  2. customAfter removing the volatiles, brine
  3. additionwas added (50 mL)
  4. extractionthe solution was extracted with ethyl acetate (3×40 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f77142437d2d4f5f8d7e0435a0b68190
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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