tert-Butyl 4-formylpiperidine-1-carboxylate → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	tert-Butyl 4-formylpiperidine-1-carboxylate	HCID 1514430	—
Reactant	HCID 178418573	HCID 178418573	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate	HCID 21989903	90.2%

Reaction Conditions

Temperature	-78 °C

Reaction Steps

Placed tert-butyl 4-formylpiperidine-1-carboxylate (2.00 g, 9.38 mmol) in THF (40 mL) and cooled to −78° C. Slowly added methylmagnesium bromide (3.44 mL, 10.3 mmol) stirred for 1 hour. Slowly added saturated ammonium chloride and extracted with CH2Cl2. Concentrated and redissolved in 5% MeOH in CH2Cl2. Added ether and filtered off solids. Concentrate filtrate to give the title compound (1.94 g, 90.2% yield)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08022223B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-e866eee4ded14399b36a69408e9cf124
Source note	uspto-grants-2011_09