2-Benzyloxirane, (R)- → 1'-[(2R)-2-hydroxy-3-phenylpropyl]-8-methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

Participants

Role	Name	HCID	Charge
Reactant	2-Benzyloxirane, (R)-	HCID 11018916	—
Reactant	8-Methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione	HCID 57661878	—
Product	1'-[(2R)-2-hydroxy-3-phenylpropyl]-8-methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione	HCID 57661998	—

Reaction Steps

Compound 204 was synthesized using 8-methoxyspiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, (2R)-2-benzyloxirane and conditions outlined in procedure Y. M.p.=145-147° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.73 (d, J=8.6 Hz, 1H), 7.38 (d, J=7.6 Hz, 1H), 7.34 (d, J=2.8 Hz, 1H), 7.31 (d, J=3.0 Hz, 1H), 7.28-7.12 (m, 4H), 4.43 (d, J=4.7 Hz, 1H), 3.84 (s, 3H), 3.03 (s, 2H), 2.80-2.68 (m, 2H), 2.58 (dd, J=7.4, 14.0 Hz, 1H), 2.47-2.26 (m, 3H), 1.99-1.90 (m, 2H), 1.87-1.72 (m, 2H). LCMS: 466 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08039503B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-179910ceeb0c495ca98912873bacfdcb
Source note	uspto-grants-2011_10