Hydrochloric Acid → HCID 68825322, compound

HRID 1982930Notes

Reaction equation

HRID 1982930 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[CH:21]=[CH:20][C:19](C(OCC)=O)=[CH:18][CH:17]=2)O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:27].[Na+].Cl.[CH3:30][OH:31]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:30]([OH:31])=[O:27])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 57712341HCID 57712341, compound

Product 1

HCID 68825322HCID 68825322, compound

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 4-[(4-ethoxycarbonyl-phenyl-)hydroxy-methyl]-piperidine-1-carboxylic acid tert-butyl ester (2.145 g, 6.18 mmol) in methanol (30 mL) is added 10 mL of 1N aqueous NaOH and the reaction is heated in a 50° C. bath for 1 hour. The reaction is cooled to 0° C. and carefully acidified with 1N aqueous HCl. The reaction is extracted with dichloromethane (DCM), dried over MgSO4, filtered and concentrated to give 1.34 grams of 4-(carboxy-benzyl)-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureThe reaction is cooled to 0° C.
  2. extractionThe reaction is extracted with dichloromethane (DCM)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-12cfb1c4877341a684d3ba8500d6c13a
Source dataset
uspto-grants-2009_06
Patent number
US07541368B2

Reaction notes

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