Methanol → 2-(1-Pyrrolidinyl)-4-(hydroxymethyl)thiazole

HRID 1861171Notes

Reaction equation

HRID 1861171 reaction equation
[N:1]1([C:6]2[S:7][CH:8]=[C:9]([C:11](OCC)=[O:12])[N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CO>C(Cl)(Cl)Cl>[N:1]1([C:6]2[S:7][CH:8]=[C:9]([CH2:11][OH:12])[N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 13339674Ethyl 2-(pyrrolidin-1-yl)thiazole-4-carboxylate

Product 1

HCID 187591502-(1-Pyrrolidinyl)-4-(hydroxymethyl)thiazoleYield 4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Using the procedure of Example 11C but replacing ethyl 2-(4-morpholinyl)thiazole-4-carboxylate with ethyl 2-(1-pyrrolidinyl)thiazole-4-carboxylate provided, after silica gel chromatography using 2-4% methanol in chloroform, the desired compound (Rf 0.26, 4% methanol in chloroform) in 53% yield. 1 H NMR (CDCl3) δ 2.04 (m, 4 H), 2.75 (br, 1 H), 3.45 (m, 4 H), 4.56 (s, 2 H), 6.32 (s, 1 H). Mass spectrum: (M+H)+=185.

Workup

  1. customprovided

Sources & evidence

ORD record
ord-ca3cd9c69d3f49dc878fcc5f253ba7a7
Source dataset
uspto-grants-2003_03
Patent number
US06531610B1

Reaction notes

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