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

HRID 17864

反応式

HRID 17864 の反応式
[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

参加物

6

反応物 3

HCID 4498Nipecotic AcidHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-41a63700f6cc44a0b5ecf557890effc5
出典データセット
uspto-grants-2010_06
特許番号
US07741322B2

関連ノート

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