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

HRID 1665393Notes

Reaction equation

HRID 1665393 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][C:12]3([O:19][C:18]4[C:20]5[C:25]([C:26](=[O:29])[C:27](=[O:28])[C:17]=4[S:16][CH2:15]3)=[CH:24][CH:23]=[CH:22][CH:21]=5)[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.[C:30]([C:34]1[CH:44]=[CH:43][C:37]([O:38][CH2:39][C@@H:40]2[CH2:42][O:41]2)=[CH:36][CH:35]=1)([CH3:33])([CH3:32])[CH3:31].CCN(C(C)C)C(C)C>>[C:30]([C:34]1[CH:44]=[CH:43][C:37]([O:38][CH2:39][C@@H:40]([OH:41])[CH2:42][N:3]2[CH2:4][CH2:5][CH:6]([N:9]3[CH2:14][CH2:13][C:12]4([O:19][C:18]5[C:20]6[C:25]([C:26](=[O:29])[C:27](=[O:28])[C:17]=5[S:16][CH2:15]4)=[CH:24][CH:23]=[CH:22][CH:21]=6)[CH2:11][CH2:10]3)[CH2:7][CH2:8]2)=[CH:36][CH:35]=1)([CH3:31])([CH3:32])[CH3:33]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 7193734-tert-Butylphenyl glycidyl ether, (+)-HCID 674394441'-Piperidin-4-ylspiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione bis-hydrochloride

Product 1

HCID 576619461'-{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

Procedure

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].

Sources & evidence

ORD record
ord-c345fca80fd24399ad64e8832ae3267f
Source dataset
uspto-grants-2011_10
Patent number
US08039503B2

Reaction notes

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