Hydrochloric Acid → (S)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride

HRID 751617ノート

反応式

HRID 751617 の反応式
C(OC(=O)[NH:7][C@@H:8]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[ClH:27].O1CCOCC1>CO>[ClH:27].[NH2:7][C@@H:8]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[C:9]([N:11]1[CH2:12][CH2:13][CH:14]([OH:17])[CH2:15][CH2:16]1)=[O:10]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 10808894[(S)-1-(4-Fluoro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

生成物 1

HCID 67278381(S)-2-Amino-3-(4-fluoro-phenyl)-1-(4-hydroxy-piperidin-1-yl)-propan-1-one hydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Route A: To a solution of [1 (S)-(4-fluorobenzyl)-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]carbamic acid tert-butyl ester (Preparation 19, 11.6 g, 31.7 mmol) in methanol (40 mL) was added hydrochloric acid in dioxane (24 mL, 4N, 95.0 mmol) and the reaction mixture stirred at rt for 6 h. The solvent was removed in vacuo and the residue was dissolved in water (100 mL) and extracted into ethyl acetate (2×50 mL). The aqueous phase was evaporated to dryness to give the title compound as a white solid. δH (D2O): 0.52–0.63 (0.5H, m), 1.12–1.23 (0.5H, m), 1.26–1.38 (1H, m), 1.42–1.50 (0.5H, m), 1.59–1.69 (0.5H, m), 1.72–1.82 (1H, m), 2.61–2.71 (0.5H, m), 2.91–3.15 (4H, m), 3.33–3.47 (1H, m), 3.69–3.78 (1H, m), 3.88–3.96 (1H, m), 4.60–4.72 (1H, m), 7.02–7.11 (2H, m), 7.14–7.26 (2H, m).

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (100 mL)
  3. extractionextracted into ethyl acetate (2×50 mL)
  4. customThe aqueous phase was evaporated to dryness

出典と根拠

ORDレコード
ord-ae13250f2e7b44b4b50e3af7bbf64cf3
出典データセット
uspto-grants-2008_07
特許番号
US07405210B2

反応ノート

読み込み中…