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

HRID 506655Notes

Reaction equation

[CH3:1][C@H:2]1[N:7]2[C:8]3[CH:9]=[CH:10][C:11]([O:15][CH2:16][CH2:17][CH2:18][N:19]4C[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=[O:25])[NH:4][CH2:3]1.[OH:26][C@@H]1CCNC1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[OH:26][C@@H:21]1[CH2:22][CH2:23][N:19]([CH2:18][CH2:17][CH2:16][O:15][C:11]2[CH:10]=[CH:9][C:8]3[N:7]4[C@H:2]([CH3:1])[CH2:3][NH:4][C:5](=[O:25])[C:6]4=[CH:14][C:13]=3[CH:12]=2)[CH2:20]1

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 11430Potassium Carbonate

HCID 2759337(R)-3-Pyrrolidinol

HCID 16679613(R)-4-Methyl-8-(3-piperidin-1-yl-propoxy)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Product 1

HCID 16679221(R)-8-[3-((R)-3-Hydroxy-pyrrolidin-1-yl)-propoxy]-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-oneYield 39%

Procedure

The title compound was synthesized in analogy to example 2 from (R)-8-(3-chloro-propoxy)-4-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 9, intermediate), (R)-3-hydroxy-pyrrolidine (commercially available), potassium carbonate and potassium iodide, to give the desired product as a light brown foam (39%).

Sources & evidence

ORD record: ord-1acc1822f1be4299b92e0da052fb51af
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786109B2

Reaction notes

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