4-Piperidinecarboxylic acid → 1-Carbobenzoxy-4-piperidinecarboxylic Acid

HRID 1854352Notes

Reaction equation

HRID 1854352 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].[C:16](=O)([O:25]N1C(=O)CCC1=O)[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.CC#N>[CH2:18]([O:17][C:16]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 10340Sodium CarbonateHCID 83172Benzyl succinimido carbonate

Product 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidYield 22.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of piperidine-4-carboxylic acid (10.0 g, 77.4 mmol) and Na2CO3 (8.21 g, 77.4 mmol) in water (100 mL) was added a solution of benzyl 2,5-dioxopyrrolidin-1-yl carbonate (19.3 g, 77.4 mmol) in MeCN (100 mL). The reaction was stirred at ambient temperature for about 16 h and then concentrated under reduced pressure. The resulting aqueous solution was quenched with aqueous NH4Cl and was then extracted with EtOAc (2×100 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid as a white solid (4.56 g, 22%): LC/MS (Table 2, Method a) Rt=1.93 min; MS m/z: 262 (M−H)−.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting aqueous solution was quenched with aqueous NH4Cl
  3. extractionwas then extracted with EtOAc (2×100 mL)
  4. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38e3d388508641b4b334422a064b4094
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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