tert-butyl N-methyl-N-(3-oxopropyl)carbamate → HCID 68490529、化合物

HRID 453892ノート

反応式

HRID 453892 の反応式
[CH3:1][N:2]([CH2:10][CH2:11][CH:12]=O)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].Cl.Cl.[CH3:16][N:17]([CH3:29])[C:18]1([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.C(B)#N.[Na].CO.C(Cl)(Cl)Cl>CO.C(O)(=O)C>[CH3:16][N:17]([CH3:29])[C:18]1([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][N:21]([CH2:12][CH2:11][CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:20][CH2:19]1

参加物

7

反応物 4

HCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamateHCID 21584188Chloroform methanolHCID 67369868HCID 67369868、化合物HCID 101953985CID 101953985

生成物 1

HCID 68490529HCID 68490529、化合物収率 84.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

6.4 g (1.3 eq.) tert-butyl methyl(3-oxopropyl)carbamate were added to a solution of 7.5 g (1 eq.) N,N-dimethyl-4-(thiophen-2-yl)piperidin-4-amine bis hydrochloride in 75 ml methanol at 0° C. and the reaction mixture was stirred for 15 min at 0° C. 4.9 g (3 eq.) sodium cyanoboron hydride were then added in portions and the mixture was stirred for 90 min at room temperature. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). As the conversion was not yet complete, the pH of the reaction mixture was adjusted to 5-6 with acetic acid and the mixture was stirred for 12 h at room temperature. Once the conversion was complete, the methanol was distilled off, water was added, the mixture obtained was extracted with IPA/chloroform (2×100 ml) and the combined organic phases were dried over Na2SO4. Following removal of the solvent under reduced pressure, the residue was purified by column chromatography (silica gel; 5% MeOH/CHCl3). 8.5 g (84%) of product were obtained.

後処理

  1. stirringthe mixture was stirred for 90 min at room temperature
  2. stirringthe mixture was stirred for 12 h at room temperature
  3. distillationthe methanol was distilled off
  4. additionwater was added
  5. customthe mixture obtained
  6. extractionwas extracted with IPA/chloroform (2×100 ml)
  7. dry with materialthe combined organic phases were dried over Na2SO4
  8. customremoval of the solvent under reduced pressure
  9. customthe residue was purified by column chromatography (silica gel; 5% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-85641e1ec36a467394266724a740b276
出典データセット
uspto-grants-2013_07
特許番号
US08492559B2

反応ノート

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