Hydrochloric Acid → HCID 67036860, compound

HRID 216054Notes

Reaction equation

HRID 216054 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([C:23]([O:25]CC)=[O:24])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.Cl>[Li+].[OH-]>[CH2:1]([O:8][CH2:9][C:10]1([C:23]([OH:25])=[O:24])[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67037408HCID 67037408, compound

Product 1

HCID 67036860HCID 67036860, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 3939Lithium HydroxideSolvent

Procedure

1-tert-Butyl 4-ethyl 4-(benzyloxymethyl)piperidine-1,4-dicarboxylate from step A (0.500 g, 1.3 mmol) was dissolved in 1 N aq. LiOH (15 mL) and THF (10 mL) and was heated at 50° C. for 24 hours. The reaction mixture was acidified with 1 N HCl and extracted with Et2O. The organic extract was washed with brine, dried over MgSO4, and concentrated under vacuum to afford the title compound (0.3 g, 65%). MS (ES+) [M+H]+=349.

Workup

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-89306cfdf42a4c939c9b25e5a5e82cc8
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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