Hydrochloric Acid → 1-(tert-butoxycarbonyl)-4-(cyclopropylmethyl)piperidine-4-carboxylic acid

HRID 1777352Notes

Reaction equation

HRID 1777352 reaction equation
[OH-].[K+].C1OCCOCCOCCOCCOCCOC1.C([O:23][C:24]([C:26]1([CH2:39][CH:40]2[CH2:42][CH2:41]2)[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1)=[O:25])C.Cl>C1(C)C=CC=CC=1.O>[C:35]([O:34][C:32]([N:29]1[CH2:30][CH2:31][C:26]([CH2:39][CH:40]2[CH2:41][CH2:42]2)([C:24]([OH:25])=[O:23])[CH2:27][CH2:28]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 21061057HCID 21061057, compound

Product 1

HCID 210610451-(tert-butoxycarbonyl)-4-(cyclopropylmethyl)piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Potassium hydroxide powder (85% assay, 2.16 gm, 0.0327 mol) and 18-crown-6 ether (350 mg) are added to a solution of 4-cyclopropylmethylpiperidine-1,4-dicarboxylic acid-1-tertbutyl ester-4-ethyl ester (1.2 gm, 0.0039 mol) in dry toluene (15 mL). The reaction mixture is refluxed for 30 minutes. It is then treated with demineralized water (15 mL) at room temperature and pH is adjusted to ˜3-4 using 2N HCl (20 mL). The aqueous layer is extracted with ethyl acetate (2×15 mL) and the combined extract is dried over sodium sulfate. Removal of solvent gives 4-cyclopropylmethylpiperidine-1,4-dicarboxylic acid monotertbutyl ester.

Workup

  1. temperatureThe reaction mixture is refluxed for 30 minutes
  2. extractionThe aqueous layer is extracted with ethyl acetate (2×15 mL)
  3. extractionthe combined extract
  4. dry with materialis dried over sodium sulfate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-91febc9e8bd0414e923096815a46729d
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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