Trifluoroacetic acid → (6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,7,8,9,10,10a-octahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole

HRID 1764905Notes

Reaction equation

HRID 1764905 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:15]3=[C:16]([S:18][CH2:19][CH:20](C(OC(C)(C)C)=O)[N:14]3[C@H:13]3[CH2:28][CH2:29][N:30]=[CH:31][C@H:12]23)[CH:17]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:15]3=[C:16]([S:18][CH2:19][CH2:20][N:14]3[C@H:13]3[CH2:28][CH2:29][NH:30][CH2:31][C@@H:12]23)[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86759404tert-butyl(6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole carboxylate

Product 1

HCID 69514440(6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,7,8,9,10,10a-octahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indoleYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of tert-butyl(6bR,10aS)-5-(2,3-dichlorophenyl)-1,2,6b,9,10,10a-hexahydropyrido[4,3-b][1,4]thiazino[2,3,4-hi]indole carboxylate (10 mg, 0.21 mmol) in CH2Cl2 (4.0 mL) was added TFA (1.0 mL). The reaction mixture was stirred at 20° C. for 1 h then concentrated in vacuo. The residue was dissolved in H2O and the solution was adjusted to pH 2 by addition of 1N HCl. The aqueous layer was washed with Et2O then basified to pH 12 by addition of 50% NaOH. The solution was extracted with CHCl3, and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a pale yellow oil (79 mg, 99%). 1H NMR (CDCl3, 300 MHz) δ1.93-2.05 (br-s, 2H), 2.65-2.99 (m, 4H), 3.01-3.25 (m, 4H), 3.44-3.68 (m, 3H), 6.88 (s, 1H), 6.90 (s, 1H), 7.18 (d, J=4.6 Hz, 2H), 7.40 (t, J=4.6 Hz, 1H) ppm.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in H2O
  3. additionthe solution was adjusted to pH 2 by addition of 1N HCl
  4. washThe aqueous layer was washed with Et2O
  5. additionthen basified to pH 12 by addition of 50% NaOH
  6. extractionThe solution was extracted with CHCl3
  7. washthe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bc4a6d6f53c45ce973b631d0195ffe7
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

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