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

HRID 591191노트

반응식

HRID 591191 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-5027488f224d455bbe8b8a57b3cb5dcc
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238619B2

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