Diisopropylethylamine → 1'-{1-[(2S)-3-(4-tert-butylphenoxy)-2-hydroxypropyl]piperidin-4-yl}spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-tert-Butylphenyl glycidyl ether, (+)-	HCID 719373	—
Reactant	1'-Piperidin-4-ylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione bis-hydrochloride	HCID 67439444	—
Product	1'-{1-[(2S)-3-(4-tert-butylphenoxy)-2-hydroxypropyl]piperidin-4-yl}spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione	HCID 57661946	—

Reaction Steps

Compound 198 was synthesized using 1′-piperidin-4-ylspiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione bis-hydrochloride, (2S)-2-[(4-tert-butylphenoxy)methyl]oxirane, hunig's base and conditions outlined in procedure Y. M.p.=190-193° C.; 400 MHz 1H NMR (CDCl3) δ: 8.04-8.02 (m, 1 H), 7.74-7.67 (m, 2 H), 7.51-7.47 (m, 1 H), 7.30-7.28 (m, 2 H), 6.85-6.83 (m, 2 H), 4.30 (t, 1 H), 4.02-3.94 (m, 2 H), 3.46-3.1 (m, 3 H), 2.95-2.92 (m, 4 H), 2.82 (d, 2 H), 2.72 (t, 2 H), 2.65 (bs, 2 H), 2.45 (t, 1 H), 2.19 (d, 2 H), 1.98-1.93 (m, 6 H), 1.29 (s, 9 H); LCMS: 591 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08039503B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-c345fca80fd24399ad64e8832ae3267f
Source note	uspto-grants-2011_10