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

HRID 23713

반응식

HRID 23713 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-14a1a40fce874bbd8bc183963b270f71
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852731B2

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