Tetrahydrofuran → N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-2,2-dithien-2-ylacetamide

HRID 1724669

반응식

HRID 1724669 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:7]([OH:9])=O.[C:15]([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)(N1C=CN=C1)=O.[N-]1C=CN=C1.[CH2:32]1[CH2:36]OC[CH2:33]1>CCOCC>[N:22]12[CH2:15][CH2:36][CH:32]([CH2:33][CH2:23]1)[C@@H:25]([NH:24][C:7](=[O:9])[CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[CH2:26]2

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 20443Di(2-thienyl)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 3386966Imidazolate

생성물 1

HCID 9996901N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-2,2-dithien-2-ylacetamide

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

2,2-dithien-2-ylacetic acid was produced by hydrolysis of 2,2-dithien-2-ylacetic acid methyl ester, previously prepared as described in F. Leonard and 1. Ehranthal, J. Am. Chem. Soc, (1951), Vol 73, pag 2216. 1.2 g (0.0054 mol) of 2,2-dithien-2-ylacetic acid were dissolved in 25 ml of THF. To this solution were added 0.96 g (0.00594 mol) of 1,1′-carbonyldiimidazole and the mixture was refluxed for an hour. The reaction was monitored by TLC following the formation of the imidazolide. When the reaction was completed 0.75 g (0.00594 mol) of (3R)-aminoquinuclidine were added. The reaction mixture was refluxed for 16 h, cooled, diluted with ether and washed with water. The organic layer was extracted with HCl 2N, the acid solution basified with K2CO3 and extracted with CHCl3. The organic phase was dried over Na2SO4 and the solvent was evaporated to obtain 0.60 g of an oil which was purified by column chromatography (silica gel, CHCl3:MeOH:NH4OH 90:10:1 as eluent). Appropriate fractions were combined and evaporated to give 0.31 g of the title product (17.3%).

후처리

  1. custompreviously prepared
  2. temperaturethe mixture was refluxed for an hour
  3. additionwere added
  4. temperatureThe reaction mixture was refluxed for 16 h
  5. temperaturecooled
  6. washwashed with water
  7. extractionThe organic layer was extracted with HCl 2N
  8. extractionextracted with CHCl3
  9. dry with materialThe organic phase was dried over Na2SO4
  10. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-56f6ce8d235e45218d8b5ae90005009b
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07488735B2

연결된 노트

불러오는 중…