tert-butyl N-methyl-N-(3-oxopropyl)carbamate → HCID 68490529, 화합물

HRID 1500341노트

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HRID 1500341 반응식
[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

참가 물질

7

반응물 4

HCID 10442454tert-butyl N-methyl-N-(3-oxopropyl)carbamateHCID 21584188Chloroform methanolHCID 67369868HCID 67369868, 화합물HCID 101953985CID 101953985

생성물 1

HCID 68490529HCID 68490529, 화합물수율 84.1%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7980c59463764d378caaf4f9efea57e1
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206156B2

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