Ethyl 1,2,3,4-tetrahydro-3-isoquinolinecarboxylate → N-(N'-acetylsarcosyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic ethyl ester

HRID 2231818Notes

Reaction equation

HRID 2231818 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][NH:7]1)=[O:5])[CH3:2].[C:16]([N:19]([CH2:21][C:22](O)=[O:23])[CH3:20])(=[O:18])[CH3:17]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][N:7]1[C:22](=[O:23])[CH2:21][N:19]([C:16](=[O:18])[CH3:17])[CH3:20])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 652898Ethyl 1,2,3,4-tetrahydro-3-isoquinolinecarboxylateHCID 10975514N-Acetyl-N-methylglycine

Product 1

HCID 21284821N-(N'-acetylsarcosyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic ethyl ester

Reagents, catalysts & solvents 1

HCID 131709914Lindlars catalystCatalyst

Procedure

This compound can be prepared by condensing 1,2,3,4-tetrahydroisoquinoline-3-carboxylic ethyl ester with N-acetylsarcosine according to the above-described methods; the corresponding acid can be prepared via catalytic hydrogenation of the product ester using Lindlar's catalyst or via base hydrolysis.

Workup

  1. customvia base hydrolysis

Sources & evidence

ORD record
ord-c0644c28721d421f812e0e1e7a458b3e
Source dataset
uspto-grants-1988_11
Patent number
US04785003

Reaction notes

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