Acetic Acid → tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate

HRID 43339

反応式

HRID 43339 の反応式
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[F:15][C:16]1[CH:17]=[C:18]([NH:19][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH:20]=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 97423-FluoroanilineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 23137591tert-Butyl 4-(3-fluoroanilino)piperidine-1-carboxylate収率 82%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (1.91 g, 9.53 mmol), 3-fluoroaniline (1.06, 9.53 mmol) and acetic acid (0.55 ml, 9.53 mmol) in 1,2-DCE (50 ml) was stirred at room temperature overnight. Sodium tri(acetoxy)borohydride (2.82 g, 13.3 mmol) was then added, stirred for 8 hrs and then allowed to stand at room temperature. The reaction mixture was diluted with DCM and washed with NaHCO3 solution, dried over MgSO4 and then concentrated to give the product which was purified by column chromatography. Elution with 0-40% EtOAc/pentane gave the title compound as a white solid (2.3 g). δH (CDCl3, 250 MHz) 7.08 (1H, q), 6.35 (3H, m), 4.04 (1H, br s), 3.65 (1H, br s), 3.38 (1H, m), 2.92 (2H, m), 2.02 (2H, m), 1.47 (9H, s), 1.34 (2H, m).

後処理

  1. customto stand at room temperature
  2. washwashed with NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give the product which
  6. customwas purified by column chromatography
  7. washElution with 0-40% EtOAc/pentane

出典と根拠

ORDレコード
ord-ed5e4844a6594da5b9d1c7dabd6a94e7
出典データセット
uspto-grants-2013_09
特許番号
US08536182B2

関連ノート

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