Ethanol hydrochloride → (6bR,10aS)-1,2,6b,7,8,9,10,10a-octahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole 3,3-dioxide hydrochloride

HRID 1764911Notes

Reaction equation

[CH2:1]1[N:11]2[C:12]3[C:8]([C@@H:9]4[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13][C@@H:10]42)=[CH:7][CH:6]=[CH:5][C:4]=3[S:3](=[O:25])(=[O:24])[CH2:2]1.[ClH:26].C(O)C>>[ClH:26].[CH2:1]1[N:11]2[C:12]3[C:8]([C@@H:9]4[CH2:16][NH:15][CH2:14][CH2:13][C@@H:10]42)=[CH:7][CH:6]=[CH:5][C:4]=3[S:3](=[O:24])(=[O:25])[CH2:2]1

Participants

Reactant 2

HCID 21887872Ethanol hydrochloride

HCID 131724390HCID 131724390, compound

Product 1

HCID 69513856(6bR,10aS)-1,2,6b,7,8,9,10,10a-octahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole 3,3-dioxide hydrochlorideYield 73%

Conditions

Temperature: 0 °C

Procedure

The tert-butyl(6bR,10aS)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate 3,3-dioxide (130 mg) was mixed with cold ethanol hydrochloride (4M) (5 mL), and the solution was stirred for 10 min at 0° C. The solvent was removed under reduced pressure and the residue was dissolved in hot acetonitrile with a small amount of methanol. Upon cooling to room temperature, the title compound (78 mg, 73%) was obtained as white crystalline material. 1H NMR (CD3OD, 500 MHz) δ2.13-2.22 (m, 1H), 2.23-2.32 (m, 1H), 2.88 (t, 1H, J=11.3 Hz), 3.19-3.35 (m, 4H), 3.45-3.66 (m, 4H), 3.78-3.88 (m, 2H), 6.92 (t, 1H, J=7.8 Hz), 7.39 (d, 1H, J=7.8 Hz), 7.49 (d, 1H, J=8.5 Hz) ppm. CIMS (Methane) m/z=265 [C13H16N2O2S+H]+.

Workup

customThe solvent was removed under reduced pressure
dissolutionthe residue was dissolved in hot acetonitrile with a small amount of methanol
temperatureUpon cooling to room temperature

Sources & evidence

ORD record: ord-0a73327855e446b08b3987ced1d9d257
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039679E1

Reaction notes

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