3-(2-(Trifluoromethyl)phenyl)-2-propenoic acid → (+/-)-(E)-2-(trimethylsilyl)ethyl 7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-ylcarbamate

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	3-(2-(Trifluoromethyl)phenyl)-2-propenoic acid	HCID 74939	—
Edukt	Diisopropylethylamine	HCID 81531	—
Edukt	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Edukt	(+/-)-2-(Trimethylsilyl)ethyl 7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-3-ylcarbamate	HCID 67224539	—
Lösungsmittel	Dichloromethane	HCID 6344	—
Produkt	(+/-)-(E)-2-(trimethylsilyl)ethyl 7-bromo-1'-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-3-ylcarbamate	HCID 67223014	47,3%

Reaktionsschritte

To a stirred solution of (±)-2-(trimethylsilyl)ethyl 7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-ylcarbamate (23 mg, 0.056 mmol), ortho-(trifluoromethyl)cinnamic acid (16 mg, 0.074 mmol) and i-Pr2NEt (0.027 mL, 0.15 mmol) in CH2Cl2 (3 mL) was added solid HATU (28 mg, 0.0.074 mmol). The mixture was stirred overnight at rt and evaporated to leave a residue which was purified by preparative HPLC to afford (±)-(E)-2-(trimethylsilyl)ethyl 7-bromo-1′-(3-(2-(trifluoromethyl)phenyl)acryloyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-ylcarbamate (16.5 mg, 47%). LC-MS Method 1 tR=2.37 min, m/z=623, 625.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08383629B2
Quelldatensatz	uspto-grants-2013_02
ORD ID	ord-380bef39935f46e6bc976562601e0820
Quellennotiz	uspto-grants-2013_02