Nipecotic Acid → 1-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

HRID 17864

반응식

HRID 17864 반응식
[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1.[OH-].[Na+].[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.O1CCCC1>[CH2:12]([O:19][C:20]([N:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([OH:6])=[O:5])[CH2:2]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 4498Nipecotic AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2회

생성물 1

HCID 2343391-((Benzyloxy)carbonyl)piperidine-3-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

실험 절차

To an ice cooled solution of nipecotic acid (10.0 g, 77.5 mmol), sodium hydroxide (3.4 g, 85 mmol), and tetrahydrofuran (50 mL) in water (100 mL) was added by simultaneous dropwise addition benzylchloroformate (13.3 mL, 93 mmol) in tetrahydrofuran (50 mL) and sodium hydroxide (3.4 g, 85 mmol) in water (50 mL). Warmed slowly to room temperature. After 24 hours tetrahydrofuran was removed in vacuo and the resulting aqueous mixture acidified with 3 N hydrochloric acid and extracted with dichloromethane (3×). The combined organic portions were dried with anhydrous magnesium sulfate. Filtration followed by evaporation of the filtrate in vacuo gave the titled compound. 1HNMR (CHCl3, 300 MHz) □ 7.45-7.20 (m, 5H); 5.14 (m, 2H); 4.21 (br s, 1H); 3.96 (m, 1H), 3.15 (br s, 1H); 2.93 (m, 1H); 2.51 (m, 1H); 2.09 (m, 1H); 1.80-1.60 (m, 2H); 1.50 (m, 1H) ppm.

후처리

  1. customAfter 24 hours tetrahydrofuran was removed in vacuo
  2. extractionextracted with dichloromethane (3×)
  3. dry with materialThe combined organic portions were dried with anhydrous magnesium sulfate
  4. filtrationFiltration
  5. customfollowed by evaporation of the filtrate in vacuo

출처 및 근거

ORD 기록
ord-41a63700f6cc44a0b5ecf557890effc5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741322B2

연결된 노트

불러오는 중…