Trifluoroacetic acid → (6bS,10aR)-1,2,6b,7,8,9,10,10a-octahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole 3-oxide

HRID 1764912Notes

Reaction equation

HRID 1764912 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:24])[CH2:2]1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[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])[CH2:2]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 131724391tert-butyl(6bS,10aR)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate 3-oxide

Product 1

HCID 69513886(6bS,10aR)-1,2,6b,7,8,9,10,10a-octahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole 3-oxideYield 35.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound (28 mg, 17%) was prepared by treatment of tert-butyl(6bS,10aR)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole-8(7H)-carboxylate 3-oxide (110 mg) with excess TFA in CH2Cl2 at 0 C. followed by treatment with 1 N aq. NaOH. 1H NMR (300 MHz, CDCl3) 1.79-1.99 (m, 1H), 2.10 (d, 1H, J=12.2 Hz), 2.39-2.57 (m, 1H), 2.72-3.01 (m, 3H), 3.01-3.22 (m, 2H), 3.22-3.51 (m, 3H), 3.61-3.72 (m, 1H), 6.69-6.89 (m, 1H), 7.17 (d, 1H, J=7.0 Hz), 7.42 (d, 1H, J=9.6 Hz) ppm. CI MS m/z=249 [C13H16N2OS+H]+.

Sources & evidence

ORD record
ord-83e415f74c9b4d70b5278616beeadafd
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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