1-Bromo-3-chloropropane → 5-(3-chloropropyl)hexahydro-1H-furo[3,4-c]pyrrole

HRID 712439노트

반응식

HRID 712439 반응식
[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][O:2]1.C([O-])([O-])=O.[K+].[K+].[Cl:15][CH2:16][CH2:17][CH2:18]Br>CC(C)=O>[Cl:15][CH2:16][CH2:17][CH2:18][N:7]1[CH2:6][CH:5]2[CH2:1][O:2][CH2:3][CH:4]2[CH2:8]1

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 21421150Hexahydro-1H-furo[3,4-c]pyrrole

생성물 1

HCID 867294855-(3-chloropropyl)hexahydro-1H-furo[3,4-c]pyrrole수율 51.7%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of hexahydro-1H-furo[3,4-c]pyrrole (0.15 g) in acetone (50 mL) was added K2CO3 (0.46 g) and 1-chloro-3-bromopropane (0.42 g, 2.0 eq) in turn. The reaction mixture was heated to reflux for 12 h and filtered. The filtrate was concentrated in vacuo and the residue was dissolved in EtOAc (100 mL). The solution was washed with water twice followed by brine once. The solution was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) EA/CH3OH) to give the title compound (0.13 g, 50.04%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 190.7 (M+1).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in EtOAc (100 mL)
  6. washThe solution was washed with water
  7. dry with materialThe solution was dried over anhydrous Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) EA/CH3OH)

출처 및 근거

ORD 기록
ord-0d551476c236425b80423284da40c02b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181277B2

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