Diisobutylaluminum hydride → (4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisobutylaluminum hydride	HCID 14487	—
Reactant	Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate	HCID 22280595	—
Solvent	Dichloromethane	HCID 6344	—
Product	(4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester	HCID 22280475	—

Reaction Conditions

Temperature	-60 °C

Reaction Steps

A solution of ethyl 2-[(N-Boc)amino]-4-thiazolecarboxylate (1 mmole) in CH2Cl2 (10 mL) was cooled to −78° C., and treated with DIBAL-H (1M, 5 mL). The reaction was stirred at −60° C. for 3 h, and quenched with a suspension of NaF/H2O (1 g/1 mL). The resulting mixture was filtered and the filtrate was concentrated to give 2-[(N-Boc)amino]-4-hydroxymethylthiazole as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06489476B1
Source dataset	uspto-grants-2002_12
ORD ID	ord-4415bc2efcc84f5f939edd22bddf5c5e
Source note	uspto-grants-2002_12