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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1665383Generated: November 1, 2026

2-Benzyloxirane, (S)- → 9-bromo-1'-[(2S)-2-hydroxy-3-phenylpropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione

https://huagongshe.com/reaction/1665383

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Benzyloxirane, (S)-HCID 11018915—
Reactant9-Bromospiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dioneHCID 57661842—
Product9-bromo-1'-[(2S)-2-hydroxy-3-phenylpropyl]spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dioneHCID 57661914—

Reaction Steps

Compound 188 was synthesized using 9-bromospiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione, (2S)-2-benzyloxirane and conditions outlined in procedure Y. M.p.=82-83° C.; 400 MHz 1H NMR (DMSO-d6) δ: 7.82-7.76 (m, 3H), 7.29-7.21 (m, 4H), 7.19-7.14 (m, 1H), 4.47-4.44 (m, 1H), 3.89-3.82 (m, 1H), 3.08 (s, 2H), 2.82-2.69 (m, 3H), 2.63-2.54 (m, 1H), 2.42-2.27 (m, 4H), 2.20-1.94 (m, 2H), 1.86-1.77 (m, 2H); LCMS: 514 [M+H].

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08039503B2
Source datasetuspto-grants-2011_10
ORD IDord-3367cfe9abf14610ac8a0f2101079e15
Source noteuspto-grants-2011_10