Formaldehyde → (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(hydroxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Formaldehyde	HCID 712	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	tert-Butyl (6S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}-4-methyl-3-oxo-1,2,3,6-tetrahydropyridine-1-carboxylate	HCID 89852373	—
Catalyst	Tributylphosphine	HCID 13831	—
Solvent	Methanol	HCID 887	—
Solvent	Dichloromethane	HCID 6344	—
Product	(S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4-(hydroxymethyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate	HCID 89852514	102%

Reaction Steps

To a solution of (S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-5-oxo-5,6-dihydropyridine-1(2H)-carboxylate (Intermediate 7, 18 g, 52.71 mmol) in a mixture of DCM (900 mL) and MeOH (350 mL) was added successively formaldehyde (42.8 mL, 527.06 mmol) and tributylphosphine (0.692 mL, 3.16 mmol) at rt. The solution was stirred at room temperature for 2-3 hr until TLC (4:1 Hex/EA) showed that the reaction was complete. It was concentrated under reduced pressure and purified by 120 g silica gel column (0-50% Hex/EA) to afford the title compound (20.00 g, 102%) as an oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09309245B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-d974857650d74f46af8380d29e833e48
Source note	uspto-grants-2016_04