Methylamine → tert-Butyl (2-[1-(4-chlorophenyl)cyclobutyl]-2-{3-[(methylamino)methyl]phenyl}ethyl)carbamate

HRID 331693노트

반응식

HRID 331693 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=O)[CH:23]=3)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:30][NH2:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.[OH-].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:31][CH3:30])[CH:23]=3)[CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86663504tert-Butyl {2-[1-(4-chlorophenyl)cyclobutyl]-2-(3-formylphenyl)ethyl}carbamate

생성물 1

HCID 68077950tert-Butyl (2-[1-(4-chlorophenyl)cyclobutyl]-2-{3-[(methylamino)methyl]phenyl}ethyl)carbamate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

tert-Butyl {2-[1-(4-chlorophenyl)cyclobutyl]-2-(3-formylphenyl)ethyl}carbamate (0.19 g, 0.459 mmol) was dissolved in dichloromethane and methylamine (1.15 ml, 2.295 mmol) was added. The reaction mixture was stirred at room temperature for 1 h. Sodium triacetoxyborohydride (0.146 g, 0.689 mmol) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with sodium hydroxide (1 N) and extracted with ethyl acetate. The combined extracts were dried (magnesium sulfate), concentrated in vacuo and the crude product purified by flash chromatography (silica, dichloromethane, methanol). Yield: 0.11 g (0.256 mmol, 56%)

후처리

  1. stirringThe reaction mixture was stirred at room temperature over night
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. customthe crude product purified by flash chromatography (silica, dichloromethane, methanol)

출처 및 근거

ORD 기록
ord-6c5d5b6fcfdc44ada6b03f37884877b5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877794B2

반응 노트

불러오는 중…