2-Benzyloxirane, (R)- → 9-chloro-1'-[(2R)-2-hydroxy-3-phenylpropyl]spiro[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	9-Chlorospiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione	HCID 57662060	—
Product	9-chloro-1'-[(2R)-2-hydroxy-3-phenylpropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione	HCID 57661947	—

Reaction Steps

Compound 194 was synthesized using 9-chlorospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, (2R)-2-benzyloxirane and conditions outlined in procedure Y. M.p.=92-93° C., 400 MHz 1H NMR (CDCl3) δ: 8.00-7.97 (d, J=8.21 Hz, 1H), 7.668-7.663 (d, J=1.95 Hz, 1H), 7.46-7.43 (dd, J=1.95, 8.21 Hz, 1H), 7.33-7.23 (m, 5H), 4.09-3.94 (m, 1H), 3.33 (br s, 1H), 2.88-2.82 (m, 4H), 2.75-2.70 (m, 3H), 2.52-2.41 (m, 3H), 2.14-2.11 (d, J=12.9 Hz, 2H), 1.94-1.80 (m, 2H); LCMS: 470 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08039503B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-2299e4f4fa894c46b9405aefd7689baf
Source note	uspto-grants-2011_10