Hydrochloric Acid → 1-((Tert-butoxy)carbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid

HRID 655946ノート

反応式

HRID 655946 の反応式
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][CH2:5][C:4]([C:11]([O:13]C)=[O:12])([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.[Li+].[OH-].Cl>C1COCC1.CO>[C:18]([O:17][C:15]([N:1]1[CH2:2][CH2:3][C:4]([C:7]([O:9][CH3:10])=[O:8])([C:11]([OH:13])=[O:12])[CH2:5][CH2:6]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 579202841-Tert-butyl 4,4-dimethyl piperidine-1,4,4-tricarboxylate

生成物 1

HCID 579202821-((Tert-butoxy)carbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid収率 80%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a solution of 1-tert-butyl 4,4-dimethyl piperidine-1,4,4-tricarboxylate (6.2 g, 20.5 mmol) in THF (11 mL) and CH3OH (11 mL) was added aqueous LiOH (2 N, 11 mL, 22 mmol, 1.1 equiv.). The reaction mixture was stirred at 80° C. for 1 h. The reaction mixture was neutralized with HCl (1N) and was concentrated to dryness. The residue was dissolved in ethyl acetate and dried over Na2SO4 and concentrated to give 1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidine-4-carboxylic acid (4.7 g, 80%), which was used without further purification. LRMS (M+H+-Boc) m/z 188.0.

後処理

  1. concentrationwas concentrated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-0eb8ca6bc06144f494b88536b05791b2
出典データセット
uspto-grants-2011_12
特許番号
US08071625B2

反応ノート

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