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

HRID 253064

反応式

HRID 253064 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 538083811-Boc-4-phenyl-4-piperidinedicarboxylic acid methyl ester収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-397eb00a97bd445d9ef86bb198f7b2a2
出典データセット
uspto-grants-2011_01
特許番号
US07872006B2

関連ノート

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