Methanol → 1-Boc-4-phenyl-4-piperidinedicarboxylic acid methyl ester

HRID 253064

반응식

HRID 253064 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:20]([OH:22])=[O:21])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[C:25](=O)([O-])O.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:20]([O:22][CH3:25])=[O:21])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid

생성물 1

HCID 538083811-Boc-4-phenyl-4-piperidinedicarboxylic acid methyl ester수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-tert-butoxycarbonyl-4-carboxy-4-phenylpiperidine (1.53 g) in tetrahydrofuran (2 mL)-methanol (2 mL) was added dropwise 2N (trimethylsilyl)diazomehane-diethyl ether solution (8.8 mL) at room temperature and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution and the mixture was stirred and extracted with chloroform. The extract was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=90/10 to 85/15) to obtain 1-tert-butoxycarbonyl-4-methoxycarbonyl-4-phenylpiperidine (1.31 g, yield: 82%) as a colorless solid.

후처리

  1. stirringthe mixture was stirred
  2. extractionextracted with chloroform
  3. dry with materialThe extract was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resultant crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=90/10 to 85/15)

출처 및 근거

ORD 기록
ord-397eb00a97bd445d9ef86bb198f7b2a2
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872006B2

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