Glycolaldehyde → HCID 69800209, compound

HRID 895337Notes

Reaction equation

HRID 895337 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[OH-].[OH-].[CH:14]([C:17]1[CH:18]=[C:19]([B+2])[CH:20]=[CH:21][CH:22]=1)([CH3:16])[CH3:15].[CH:24](=O)[CH2:25][OH:26]>>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([CH:24]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([CH:14]([CH3:16])[CH3:15])[CH:18]=2)[CH2:25][OH:26])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 756GlycolaldehydeHCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 178419129HCID 178419129, compound

Product 1

HCID 69800209HCID 69800209, compound

Procedure

Following the procedure described in Petasis N. A. et al. in Tetrahedron (1997), 53, 16463-16470, ethyl-N-piperazine carboxylate was reacted with 3-isopropylphenyl-boron dihydroxide in the presence of glycolaldehyde to provide 4-[2-hydroxy-1-(3-isopropyl-phenyl)-ethyl]-piperazine-1-carboxylic acid ethyl ester (compound 18). The compounds listed in Table III were obtained by the same method.

Sources & evidence

ORD record
ord-e5a6f9a438594c738a50f8b83d4cc322
Source dataset
uspto-grants-2005_07
Patent number
US06916797B2

Reaction notes

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