(R)-3-Pyrrolidinol → 8-[3-((R)-3-Hydroxy-pyrrolidin-1-yl)-propoxy]-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 506647Notes

Reaction equation

HRID 506647 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[CH2:20][CH2:21][NH:22][C:23](=[O:24])[C:15]4=[CH:14][C:13]=3[CH:12]=2)[CH2:6][CH2:5]C[CH2:3][CH2:2]1.[OH:25][C@@H]1CCNC1>>[OH:25][C@@H:3]1[CH2:5][CH2:6][N:1]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[CH2:20][CH2:21][NH:22][C:23](=[O:24])[C:15]4=[CH:14][C:13]=3[CH:12]=2)[CH2:2]1

Participants

3

Reactant 2

HCID 2759337(R)-3-PyrrolidinolHCID 166795198-(3-(piperidin-1-yl)propoxy)-3,4-dihydropyrazino[1,2-a]indol-1(2H)-one

Product 1

HCID 166796108-[3-((R)-3-Hydroxy-pyrrolidin-1-yl)-propoxy]-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-oneYield 22%

Procedure

The title compound was synthesized in analogy to example 2, from 8-(3-chloro-propoxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 2, intermediate) and (R)-3-hydroxypyrrolidine (commercially available), to give the desired product as colorless solid (22%).

Sources & evidence

ORD record
ord-d505441bedb44d68b662d691c7bbfe3f
Source dataset
uspto-grants-2010_08
Patent number
US07786109B2

Reaction notes

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