반응 #218071

반응 방정식

cyclopentene oxide

tyramine

→

title compound

4-[2-(2-Hydroxycyclopentylamino)ethyl]phenol

용매

EtOAc

NaOH

반응 조건

후처리

1. 1
   workup.WAITat 100° C. for 18 hours
2. 2
   기타Quench
3. 3
   기타the reaction with saturated aqueous NH4Cl (40 mL)
4. 4
   기타Separate the layers
5. 5
   workup.STIRRINGafter shaking
6. 6
   세척Wash the organic layer with H2O and brine (50 mL each)
7. 7
   추출Back-extract the aqueous layers with CH2Cl2, EtOAc and CH2Cl2 (50 mL each)
8. 8
   농축concentrate
9. 9
   기타decant off the supernatant
10. 10
    workup.DISSOLUTIONDissolve the residual solid in H2O
11. 11
    추출extract it with 10:40:50 2.0 M NH3 in MeOH/CH2Cl2/EtOAc (100 mL) and 10:90 2.0 M NH3 in MeOH/CH2Cl2
12. 12
    농축concentrate
13. 13
    workup.DISSOLUTIONDissolve the residue in a small amount of MeOH
14. 14
    기타purify by flash chromatography
15. 15
    세척eluting with 10:40:50 2.0 M NH3 in MeOH/CH2CL2/EtOAc

실험 절차

Stir a mixture of cyclopentene oxide (482.0 mg, 5.73 mmol) and tyramine (943.2 mg, 6.88 mmol) in 1.0 N NaOH (20 mL) at room temperature for 64 hours, at 45-55° C. for 6 hours, and at 100° C. for 18 hours. Quench the reaction with saturated aqueous NH4Cl (40 mL) and take it up in EtOAc (50 mL). Separate the layers after shaking. Wash the organic layer with H2O and brine (50 mL each). Back-extract the aqueous layers with CH2Cl2, EtOAc and CH2Cl2 (50 mL each). Adjust the pH of the combined aqueous layers to alkaline and concentrate. Suspend the residue in 10:40:50 2.0 M NH3 in MeOH/CH2Cl2/EtOAc and decant off the supernatant. Dissolve the residual solid in H2O and extract it with 10:40:50 2.0 M NH3 in MeOH/CH2Cl2/EtOAc (100 mL) and 10:90 2.0 M NH3 in MeOH/CH2Cl2. Combine all the organic layers and concentrate. Dissolve the residue in a small amount of MeOH and purify by flash chromatography, eluting with 10:40:50 2.0 M NH3 in MeOH/CH2CL2/EtOAc to afford the title compound as a 1:3 cis/trans isomeric mixture (566 mg, 45%): MS ES+ 222.0 (M+H)+, HPLC [YMC-Pack Pro C-18 (150×4.6 min, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 5-95% over 19 min], tR=4.72 min, 76% and 6.52 min, 24%.

출처