Lithium Hydroxide → 1-Phenylpiperidine-4-carboxylic acid

HRID 1178059ノート

反応式

HRID 1178059 の反応式
[Li+].[OH-].C[O:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6]>C1COCC1.CO.O>[C:13]1([N:10]2[CH2:11][CH2:12][CH:7]([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 59559569Methyl 1-phenylpiperidine-4-carboxylate

生成物 1

HCID 30239901-Phenylpiperidine-4-carboxylic acid収率 67.3%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

LiOH (43 mg, 1.03 mmol) was added at room temperature to a stirred solution of 1-phenyl-piperidine-4-carboxylic acid methyl ester (150 mg, 0.68 mmol) in THF:MeOH:H2O (3:1:1, 3.2 mL). The resulting mixture was stirred at room temperature overnight. The MeOH and THF were evaporated and the residue was diluted with water (2 mL), acidified with citric acid solution and extracted with EtOAc. The organic layer was washed with saturated brine, dried over Na2SO4 and concentrated under reduced pressure to afford 94 mg (67.14% yield) of 1-phenyl-piperidine-4-carboxylic acid. LCMS purity: 95.98%.

後処理

  1. customThe MeOH and THF were evaporated
  2. additionthe residue was diluted with water (2 mL)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-76b049cadfc14dec8fa84d59df357cba
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

読み込み中…