Acetic Acid → 4-(N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine

HRID 2110824노트

반응식

HRID 2110824 반응식
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[CH3:16]/[C:17](=[CH:20]\[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)/[CH:18]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O.CO.ClCCl.ClCCCl>[OH-:10].[NH4+:1].[CH3:16]/[C:17](=[CH:20]\[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)/[CH2:18][NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

참가 물질

11

반응물 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 5372813alpha-METHYLCINNAMALDEHYDE

생성물 2

HCID 14923Ammonium Hydroxide수율 10%HCID 63395154-(N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine수율 128.6%

시약·촉매·용매 4

HCID 111,2-Dichloroethane용매HCID 887Methanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 4-aminomethyl-1-t-butoxycarbonylpiperidine (3.6 g, 16.8 mmol), (E)-2-methyl-3-phenylpropenal (3.9 g, 26.7 mmol), acetic acid (3.9 g, 65 mmol), and 1,2-dichloroethane (30 mL) was stirred under argon at room temperature for 30 min before sodium triacetoxyborohydride (4.1 g, 19.3 mmol) was added. After 3 h saturated aqueous sodium bicarbonate was added to make the mixture basic, then it was diluted with water and extracted with dichloromethane (three times). The combined extracts were dried (anhydrous sodium sulfate) and evaporated under vacuum prior to column chromatography (silica gel, step-wise gradient of 2% to 4% of (10% concentrated aqueous ammonium hydroxide in methanol) in dichloromethane), which provided 4-(N-(2-methyl-3-phenyl-2-(E) -propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine (3.72 g, 64% yield) as a pale yellow oil. A smaller excess of aldehyde over amine may produce optimal desired product yields when other aldehydes are used.

후처리

  1. additionwas added
  2. extractionextracted with dichloromethane (three times)
  3. dry with materialThe combined extracts were dried (anhydrous sodium sulfate)
  4. customevaporated under vacuum

출처 및 근거

ORD 기록
ord-6dc7a093d5714a33a292f6d6e2564d52
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517991B2

반응 노트

불러오는 중…