Methylamine → tert-Butyl 2-oxo-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamate

HRID 23713

反応式

HRID 23713 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=[O:4].[CH3:17][NH2:18].[C:19](=[O:30])(OC(C)(C)C)[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[O:4]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH2:2][N:18]([CH3:17])[C:19](=[O:30])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

参加物

5

反応物 3

HCID 6329MethylamineHCID 27953572-Bromo-1-(4-morpholinophenyl)ethanoneHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

生成物 1

HCID 22574343tert-Butyl 2-oxo-2-(4-morpholin-4-ylphenyl)ethyl(methyl)carbamate収率 38%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-Bromo-1-(4-morpholin-4-ylphenyl)ethanone (Tetrahedron Letters; 39, (1998), 4987-4990)(3.40 g, 11.97 mmol) was dissolved in dry THF (30 ml) under N2 and cooled in ice. A 2M solution of methylamine in THF (12 ml, 24 mmol) was added and the reaction stirred for 1 hr. The mixture was filtered and the filtrate treated with di-t-butyl carbonate (2.61 g, 12 mmol) at ice temperature. Stirring was continued for 24 hr then the solvent evaporated. Chromatography of the residue over silica gel (500 g) eluting with 1% MeOH-1% Et3N-EtOAc gave the product as a pale yellow solid (1.53 g, 38%): mp87-89°.

後処理

  1. temperaturecooled in ice
  2. filtrationThe mixture was filtered
  3. stirringStirring
  4. waitwas continued for 24 hr
  5. customthe solvent evaporated
  6. washChromatography of the residue over silica gel (500 g) eluting with 1% MeOH-1% Et3N-EtOAc

出典と根拠

ORDレコード
ord-14a1a40fce874bbd8bc183963b270f71
出典データセット
uspto-grants-2005_02
特許番号
US06852731B2

関連ノート

読み込み中…