tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylate → HCID 59900611, compound

HRID 2228751Notes

Reaction equation

HRID 2228751 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5](=[O:9])[N:4]([CH2:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[C:3]=1[CH3:21].[NH2:22][CH2:23][C@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][N:4]1[C:3]([CH3:21])=[C:2]([Cl:1])[N:7]=[C:6]([NH:22][CH2:23][C@H:24]2[CH2:28][CH2:27][CH2:26][N:25]2[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[C:5]1=[O:9])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 1512534tert-butyl (2R)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 10663926Benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate

Product 1

HCID 59900611HCID 59900611, compoundYield 80%

Procedure

The title compound was prepared by a similar method to preparation 42 from benzyl 2-[3,5-dichloro-2-methyl-6-oxo-1(6H)-pyrazinyl]acetate (preperation 17) and tert-butyl (2R)-2-(aminomethyl)-1-pyrrolidinecarboxylate [see preparation 52]. The crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (10:90) changing to (80:20) in 10% increments to afford the title compound as a clear oil, (80%).

Workup

  1. customThe crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:pentane (10:90)

Sources & evidence

ORD record
ord-dd08468159654e03951fb72b04c503d3
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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