Sulfuric Acid → HCID 59904582, compound

HRID 2303393Notes

Reaction equation

HRID 2303393 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C@:15]2([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@@H:13]([O:14]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:25]S(O)(=O)=O>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][C@:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:14])[C@@H:13]([OH:25])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86584011HCID 86584011, compound

Product 1

HCID 59904582HCID 59904582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 37.6 g (116 mmol) of (1R,6S) and (1S,6R)-6-benzyl-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid benzyl ester in 170 ml THF were added 37 ml H2SO4 (10%). The reaction mixture was stirred for 16 hours and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and extracted with sat. NaHCO3. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were washed with sat. NaHCO3, dried over MgSO4 and the solvent was removed under reduced pressure to give 40.8 g (100%, purity ˜95%) of crude (3R,4R) and (3S,4S)-4-benzyl-3,4-dihydroxy-piperidine-1-carboxylic acid benzyl ester.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. extractionextracted with sat. NaHCO3
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washthe combined organic layers were washed with sat. NaHCO3
  6. dry with materialdried over MgSO4
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9af8dd9830bc472f9fe344508519f0e5
Source dataset
uspto-grants-2002_08
Patent number
US06432985B1

Reaction notes

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