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Citric Acid → Tert-butyl 4-benzyl-4-hydroxypiperidine-1-carboxylate

HRID 2356146
Notes
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Reaction equation

HRID 2356146 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

HCID 10493799Tert-butyl 4-benzyl-4-hydroxypiperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

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-3a4be2b7f4da4e1cb364c024142cd053
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07754886B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes