Water → Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

HRID 640730노트

반응식

HRID 640730 반응식
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:15]([O:14][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][CH:6]([CH2:4][OH:3])[CH2:7]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 16091193(R)-1-Benzyl 3-ethyl piperidine-1,3-dicarboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 2776577Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Piperidine-1,3-dicarboxylic acid 1-benzyl ester 3-ethyl ester (7) (1.5 g, 5.83 mmol) was dissolved in 5.8 mL of anhydrous THF, and the reaction was stirred under N2 at −5° C. while lithium aluminum hydride dissolved in THF (7.0 mL, 1.0M) was added dropwise by addition funnel over 30 minutes. When the reaction was complete by TLC (10 min.), H2O (0.6 mL), then 10% NaOH (1.5 mL), then H2O (0.6 mL) were added, and the reaction was stirred for about 45 minutes. The salts were removed by filtration and the solution was dried with sodium sulfate, filtered, and concentrated. The crude material was purified using an ISCO CombiFlash flash column (silica, 80:20 Hexane: EtOAc to 40:60 Hexane: EtOAc) to achieve 1.24 g of pure 8 (66% yield).

후처리

  1. additionwas added dropwise by addition funnel over 30 minutes
  2. customThe salts were removed by filtration
  3. dry with materialthe solution was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified

출처 및 근거

ORD 기록
ord-d4a6b3a79b0244bbb991af599d8ea62f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692019B2

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