Lithium diisopropylamide → HCID 178455195, compound

Participants

Role	Name	HCID	Charge
Reactant	Lithium diisopropylamide	HCID 2724682	—
Reactant	(2-Bromoethoxy)-tert-butyldimethylsilane	HCID 3608067	—
Reactant	tert-butyl 4-[[2-[[(2S)-2-bicyclo[2.2.1]heptanyl]amino]-5-methyl-4-oxo-1,3-thiazol-5-yl]methyl]piperidine-1-carboxylate	HCID 178451850	—
Reactant	2-(2-bicyclo[2.2.1]heptanylamino)-5-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-1,3-thiazol-4-one	HCID 178455202	—
Product	HCID 178455195	HCID 178455195	—

Reaction Steps

The title compound was prepared according to the procedure described in the preparation of tert-butyl 4-((2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)methyl)piperidine-1-carboxylate by using 2-(bicyclo[2.2.1]heptan-2-ylamino)-5-(2-(tert-butyldimethylsilyloxy)ethyl)thiazol-4(5H)-one (630 mg, 1.71 mmol), lithium diisopropylamide (Aldrich, 2.0 M in heptane/THF/ethylbenzene, 4.27 mL, 8.55 mmol), and (2-bromoethoxy)(tert-butyl)dimethylsilane (Aldrich, 2.46 g, 10.25 mmol). The title compound was obtained as a sticky orange solid (771 mg). MS (ESI, pos. ion) m/z: 413 (M-TBDMS+2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08686011B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-6f568a38dd6b4cf8bfec61e1dfec78f5
Source note	uspto-grants-2014_04