Methyl iodide → N-[2-(1-t-Butoxycarbonylpiperidin-4-yl)phenyl]-N-methylmethanesulfonamide

HRID 1419573ノート

反応式

HRID 1419573 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:27]I>O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22266209tert-Butyl 4-{2-[(methylsulfonyl)amino]phenyl}piperidinecarboxylate

生成物 1

HCID 67553893N-[2-(1-t-Butoxycarbonylpiperidin-4-yl)phenyl]-N-methylmethanesulfonamide収率 98.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60% dispersion in mineral oil, 73.4 mg) was added to a solution of N-[2-(1-t-butoxycarbonylpiperidin-4-yl)phenyl]methanesulfonamide (650 mg) in tetrahydrofuran (50 mL) and the mixture was stirred at room temperature for 1 h. Methyl iodide (260 mg) was added and the mixture was stirred at room temperature for 36 h. The solvent was evaporated under reduced pressure, and the residue was partitioned between water and ethyl acetate (100 mL). The organic layer was separated, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as colorless solid (662 mg), δH (CDCl3) 1.48 (9H, s), 1.73 (2H, m), 1.88 (2H, m), 2.84 (2H, m), 2.97 (3H, s), 3.25 (3H, s), 3.33 (1H, m), 4.13 (2H, m), 7.21-7.36 (4H, m). m/e (ES+) 369 (MH+).

後処理

  1. stirringthe mixture was stirred at room temperature for 36 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-cf83b2e14f674cb5b6f89c391c441c76
出典データセット
uspto-grants-1999_03
特許番号
US05885999

反応ノート

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