Hydrochloric Acid → HCID 20094606, compound

HRID 654130Notes

Reaction equation

HRID 654130 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=[O:17])[C:13]([CH3:23])([O:18][Si](C)(C)C)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](=[O:17])[C:13]([OH:18])([CH3:23])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20094588HCID 20094588, compound

Product 1

HCID 20094606HCID 20094606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The thus-obtained N-benzyloxycarbonyl-3-methyl-3-trimethylsilyloxy-4-piperidone is dissolved in THF (450 mL) and concentrated hydrochloric acid (50 mL) is added. The resultant solution is stirred at 23° C. for 24 h and concentrated to an oily residue. The residue is suspended in a saturated sodium bicarbonate solution (250 mL) and the resultant suspension is extracted with ether (2×100 mL). The organics are combined, dried (MgSO4), filtered and concentrated to give crude N-benzyloxycarbonyl-3-hydroxy-3-methyl-4-piperidone as an oil: 17.2 g.

Workup

  1. concentrationconcentrated to an oily residue
  2. extractionthe resultant suspension is extracted with ether (2×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e23e09b6b27a4c3eb513e22b2ed78fa9
Source dataset
uspto-grants-1992_07
Patent number
US05130321

Reaction notes

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