Benzyl Alcohol → (3S,5R)-1-tert-Butyl 3-Methyl 5-(((Benzyloxy)carbonyl)amino)piperidine-1,3-dicarboxylate

Participants

Role	Name	HCID	Charge
Reactant	Benzyl Alcohol	HCID 244	—
Reactant	Triethylamine	HCID 8471	—
Reactant	P,P-Diphenylphosphinic azide	HCID 199401	—
Reactant	(3R,5S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-piperidine-3-carboxylic acid	HCID 11196951	—
Solvent	Toluene	HCID 1140	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	(3S,5R)-1-tert-Butyl 3-Methyl 5-(((Benzyloxy)carbonyl)amino)piperidine-1,3-dicarboxylate	HCID 70274467	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

1-(t-Butoxycarbonyl)-cis-3-methoxycarbonyl-piperidine-5-carboxylic acid (1.87 g, 6.51 mmol), benzyl alcohol (1.68 mL, 16,3 mmol), diphenyl phosphorylazide (1.47 mL, 6.83 mmol), and Et3N (0.95 mL, 6.83 mmol) were dissolved in toluene (50 mL). The solution was heated at 90° C. for 4 h. The solution was diluted with EtOAc and was washed with Sat. NaHCO3 solution, water, and brine. The organics were dried (MgSO4), filtered, and concentrated to give the title compound without further purification.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05817678
Source dataset	uspto-grants-1998_10
ORD ID	ord-51d11eb7ab1c42ee836c13bdfe997fe6
Source note	uspto-grants-1998_10