Water → HCID 59474978, compound

HRID 42537Notes

Reaction equation

HRID 42537 reaction equation
[C:1]([NH:9][C@@H:10]1[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][C@@H:11]1[C:20]([O:22]CC)=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-].O>C1COCC1>[C:1]([NH:9][C@@H:10]1[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][C@@H:11]1[C:20]([OH:22])=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 59475002HCID 59475002, compound

Product 1

HCID 59474978HCID 59474978, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(7S,8R)-Ethyl 8-benzamido-1,4-dioxaspiro[4.5]decane-7-carboxylate (740 mg, 2.22 mmol) was dissolved in THF (10 mL) at 25° C. with stirring. 0.5N LiOH (8.88 mL, 4.44 mmol) was then added thereto and the mixture stirred for 3 hours. The reaction was worked up by adding water and then removing the THF in vacuo. The remaining basic aqueous mixture was then acidified to pH=3 with 1N HCl. The aqueous mixture was extracted (2×) with methylene chloride. The methylene chloride extracts were combined, dried over sodium sulfate and concentrated to give (7S,8R)-8-benzamido-1,4-dioxaspiro[4.5]decane-7-carboxylic acid (678 mg, 2.22 mmol, 100% yield) as a white glass. MS (ESI+)=306.19 (M+H)+.

Workup

  1. stirringthe mixture stirred for 3 hours
  2. customremoving the THF in vacuo
  3. extractionThe aqueous mixture was extracted (2×) with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5eec05d37acc42d1a5da527bb6d32daf
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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