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

HRID 591191ノート

反応式

HRID 591191 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-5027488f224d455bbe8b8a57b3cb5dcc
出典データセット
uspto-grants-2016_01
特許番号
US09238619B2

反応ノート

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