1,2,3,4-Tetrahydroquinoline → HCID 59467900, compound

Participants

Role	Name	HCID	Charge
Reactant	1,2,3,4-Tetrahydroquinoline	HCID 69460	—
Reactant	N-(tert-butoxycarbonyl)glycine	HCID 78288	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 59467900	HCID 59467900	87%

Reaction Steps

To a solution of Boc-Gly-OH (80) (4.0 g, 22.83 mmol) in dry CH2Cl2 (50 mL) at 0° C. under N2 was added HATU (8.70 g, 22.9 mmol). After stirring for 15 min at r.t., 1,2,3,4-tetrahydroquinoline (2.9 mL, 23.0 mmol), and DIPEA (12 mL, 68.8 mmol) were added. The reaction was stirred for 36 h at room temperature. The reaction mixture was diluted with CH2Cl2 (100 mL) and washed with saturated NaHCO3, 5% HCl, water, and saturated NaCl. Dried over MgSO4, and filtered. The solvent was removed under reduced pressure and the product was purified by column chromatography (10-50% EtOAc in hexanes) to afford 81 as a solid (5.76 g, 87%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08916550B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-a92a0e14cf64494380020b179ea5d418
Source note	uspto-grants-2014_12