Triethylamine → [8-Benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	4-Isopropoxy-3-methylbenzoic acid	HCID 59272935	—
Reactant	4-Benzyl-2-(p-tolyl)-1-oxa-4,9-diazaspiro[5.5]undecane	HCID 68310776	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	[8-Benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone	HCID 70872696	79%

Reaction Steps

A mixture of 8-benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecane (100 mg, 0.30 mmol), 4-isopropoxy-3-methyl-benzoic acid (61 mg, 0.31 mmol) and HATU (119 mg, 0.31 mmol) was stirred in DCM (450 μL) and DMF (450 μL) for 5 minutes. Triethylamine (83 μL, 0.59 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was diluted with sat. aq. NaHCO3 (5 mL) and extracted with DCM (3×5 mL), dried over MgSO4, filtered, concentrated in vacuo and purified by silica gel column chromatography (0-100% EtOAc/hexane) to give [8-benzyl-10-(p-tolyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone as a colorless oil (120 mg, 79%). ESI-MS m/z calc. 512.3. Found 513.3 (M+1)+; Retention time: 1.86 minutes (3 min run).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08828996B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-64e2d3ec44624dfbbf8fa56207ec127f
Source note	uspto-grants-2014_09