(3S,9aS)-tert-butyl 3-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)hexahydropyrazino[2,1-c][1,4]thiazine-8(1H)-carboxylate → (3R,9aS)-tert-butyl 3-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)hexahydropyrazino[2,1-c][1,4]thiazine-8(1H)-carboxylate

HRID 1502047Notes

Reaction equation

C([S:4][CH2:5][C@H:6]1[N:11]([CH2:12][C@@H:13](O)[C:14]2[C:15]([CH3:24])=[C:16]3[C:20](=[CH:21][CH:22]=2)[C:19](=[O:23])[O:18][CH2:17]3)[CH2:10][CH2:9][N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:7]1)(=O)C.CC1C([C@@H]2SC[C@@H]3CN(C(OC(C)(C)C)=O)CCN3C2)=CC=C2C=1COC2=O>>[CH3:24][C:15]1[C:14]([C@H:13]2[S:4][CH2:5][C@@H:6]3[CH2:7][N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:9][CH2:10][N:11]3[CH2:12]2)=[CH:22][CH:21]=[C:20]2[C:16]=1[CH2:17][O:18][C:19]2=[O:23]

Participants

Reactant 2

HCID 71273525(3S,9aS)-tert-butyl 3-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)hexahydropyrazino[2,1-c][1,4]thiazine-8(1H)-carboxylate

HCID 117690268(S)-tert-butyl 3-(acetylthiomethyl)-4-((S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazine-1-carboxylate

Product 1

HCID 89633500(3R,9aS)-tert-butyl 3-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)hexahydropyrazino[2,1-c][1,4]thiazine-8(1H)-carboxylate

Procedure

Synthesis from (S)-tert-butyl 3-(acetylthiomethyl)-4-((S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazine-1-carboxylate is analagous to that for the synthesis of (3S,9aS)-tert-butyl 3-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)hexahydropyrazino[2,1-c][1,4]thiazine-8(1H)-carboxylate: 1H NMR (500 MHz, CDCl3) δ 7.78 (d, J=8.0 Hz, 1H), 7.61 (d, J=8.0 Hz, 1H), 5.28 (s, 2H), 4.41 (dd, J=2.2, 10.9 Hz, 1H), 4.04 (bm, 2H), 2.93-3.15 (m, 2H), 2.53-2.88 (m, 5H), 2.33-2.45 (m, 5H), 1.51 (s, 9H); LC/MS: [(M+1)]+=405.2.

Sources & evidence

ORD record: ord-661ecb3c51af48049840a118efc2566b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206199B2

Reaction notes

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