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

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Ethyl 2-(pyrrolidin-1-yl)thiazole-4-carboxylate	HCID 13339674	—
Solvent	Chloroform	HCID 6212	—
Product	2-(1-Pyrrolidinyl)-4-(hydroxymethyl)thiazole	HCID 18759150	4%

Reaction Steps

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. 1H NMR (CDCl3) δ 2.04 (m, 4H), 2.75 (br, 1H), 3.45 (m, 4H), 4.56 (s, 2H), 6.32 (s, 1H). Mass spectrum: (M+H)+185.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06667404B2
Source dataset	uspto-grants-2003_12
ORD ID	ord-a7a3e489b083415cae1684aabef8eed4
Source note	uspto-grants-2003_12