Citric Acid → 1,1-Dimethylethyl 4-hydroxy-4-(phenylmethyl)-1-piperidinecarboxylate

HRID 2085815Notes

Reaction equation

HRID 2085815 reaction equation
[OH:1][C:2]1([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[OH-].[Na+].[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCOCC1>[CH2:8]([C:2]1([OH:1])[CH2:7][CH2:6][N:5]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:17])[CH2:4][CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 981524-Benzyl-4-piperidinol

Product 1

HCID 104937991,1-Dimethylethyl 4-hydroxy-4-(phenylmethyl)-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-hydroxy-4-benzyl piperidine (0.66 g, 3.5 mmol) in 1M NaOH (7 mL, 7 mmol) and dioxane (5 mL) at 0° C. was treated with BOC2O (0.76 g, 3.5 mmol), warmed to room temperature, stirred for 16 hours, adjusted to pH<7 with 10% citric acid, and extracted twice with ethyl acetate. The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-382f0e773b4647b0b3a1b91325387266
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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