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

HRID 71775

반응식

HRID 71775 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+].[C:12](Cl)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>O>[CH2:15]([O:14][C:12]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

5

반응물 3

HCID 37734-Piperidinecarboxylic acidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide

생성물 1

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic Acid수율 91.2%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

Piperidine-4-carboxylic acid (64.8 g, 0.5 mol) in H2O (50 mL) was treated with NaOH (44.0 g, 1.1 mol). The reaction mixture was cooled to 0° C. and treated with CbzCl (93.8 g, 0.55 mol). The reaction mixture was stirred at ambient temperature for 4 hours and the mixture was extracted with Et2O (3 150 mL). The aqueous phase was acidified with 6 N HCl (140 mL) and extracted with EtOAc (3 200 mL). The solution was dried over MgSO4, filtered, and concentrated to afford crude piperidine-1,4-dicarboxylic acid monobenzyl ester (120 g), which was used without further purification: MS (ESI) m/z 262 [M−H]+.

후처리

  1. extractionthe mixture was extracted with Et2O (3 150 mL)
  2. extractionextracted with EtOAc (3 200 mL)
  3. dry with materialThe solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-faee25c567534f6e93cd002eea407fee
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822430B2

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