(Pyrrolidin-3-yl)methanol → benzyl N-[3-(hydroxymethyl)pyrrolidine-1-carboximidoyl]carbamate

HRID 1450706

반응식

HRID 1450706 반응식
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH2:8]([O:15][C:16]([NH:18][C:19](=[NH:22])OC)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[CH2:8]([O:15][C:16]([NH:18][C:19]([N:5]1[CH2:6][CH2:7][CH:3]([CH2:2][OH:1])[CH2:4]1)=[NH:22])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

4

반응물 2

HCID 13400657(Pyrrolidin-3-yl)methanolHCID 139267837benzyl N-(C-methoxycarbonimidoyl)carbamate

생성물 1

HCID 140379085benzyl N-[3-(hydroxymethyl)pyrrolidine-1-carboximidoyl]carbamate수율 25.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

1.01 g (0.01 mole) (3RS)-3-hydroxymethyl pyrrolidine and 2.29 g (0.011 mole) N-benzyloxycarbonyl-O-methylisourea was dissolved (the amine not very soluble) in toluene and heated to 60° C. for three hours followed by stirring at room temperature over night. The mixture was evaporated and the 1H-NMR showed that the reaction was not completed. The mixture was therefore dissolved in 15 ml acetonitrile and heated to 60° C. for three hours followed by stirring at room temperature over night. The solvebt was evaporated and the mixture was dissolved in CH2Cl2, washed once with water, dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2 /MeOH 95/5 as eluent to yield 0.70 g (25%) of the product.

후처리

  1. customThe mixture was evaporated
  2. dissolutionThe mixture was therefore dissolved in 15 ml acetonitrile
  3. temperatureheated to 60° C. for three hours
  4. stirringby stirring at room temperature over night
  5. customThe solvebt was evaporated
  6. dissolutionthe mixture was dissolved in CH2Cl2
  7. washwashed once with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-b5d3fcda3857468d87876db6ca99089a
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602253

연결된 노트

불러오는 중…