Lithium Hydroxide → N-Boc-4-cyanopiperidine-4-carboxylic acid

HRID 423062

反応式

HRID 423062 の反応式
[OH-].[Li+].[C:3]([C:5]1([C:18]([O:20]CC)=[O:19])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)#[N:4]>C1COCC1.C(OCC)C>[C:14]([O:13][C:11]([N:8]1[CH2:9][CH2:10][C:5]([C:3]#[N:4])([C:18]([OH:20])=[O:19])[CH2:6][CH2:7]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 577503761-tert-Butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate2 回

生成物 1

HCID 57750275N-Boc-4-cyanopiperidine-4-carboxylic acid収率 91%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

An aqueous solution of lithium hydroxide (2M, 39.0 mL, 77.92 mmol) was added to a stirred solution of 1-tert-butyl 4-ethyl 4-cyanopiperidine-1,4-dicarboxylate (Intermediate 7) (5.5 g, 19.48 mmol), in THF (78 mL) at 25° C. The resulting mixture was stirred at 25° C. for 3 hours and monitored by TLC. The reaction mixture was diluted with diethyl ether (150 mL), and washed with water (100 mL). The aqueous layers were combined and then acidified with citric acid (1N, 200 mL). The product was extracted into DCM. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford 1-(tert-butoxycarbonyl)-4-cyanopiperidine-4-carboxylic acid (4.50 g, 91%). This material was used in the next steps without further purification.

後処理

  1. washwashed with water (100 mL)
  2. extractionThe product was extracted into DCM
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-913c783346914bb1a7ddaff84e3acc07
出典データセット
uspto-grants-2012_01
特許番号
US08101623B2

関連ノート

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