Potassium Carbonate → HCID 67207317, compound

HRID 1894438Notes

Reaction equation

HRID 1894438 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1(C)[O:19][CH:18]([CH2:20][CH2:21]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:17][O:16]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:21][CH2:20][CH:18]([OH:19])[CH2:17][OH:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 12486297HCID 12486297, compound

Product 1

HCID 67207317HCID 67207317, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Piperazine-1-carboxylic acid tert-butyl ester (1.17 g, 6.28 mmol, Lancaster) and toluene-4-sulfonic acid 2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (1.98 g, 6.6 mmol, prepared from (2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol and tosyl chloride) and potassium carbonate (1 g, Fisher) were stirred in acetonitrile (22 mL) overnight at room temperature. After aqueous workup, the residue was purified by flash column chromatography to give 4-(3,4-dihydroxy-butyl)-piperazine-1-carboxylic acid tert-butyl ester (0.52g), which was deprotected with 1 N hydrochloric acid in methanol at 50° C. to give 4-piperazin-1-yl-butane-1,2-diol hydrochloride (360 mg).

Workup

  1. customAfter aqueous workup, the residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-c0178db973cb413d97b73d62ce5aa06a
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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