Trifluoroacetic acid → (6bR,10aS)-5-(2-chlorophenyl)-1,2,6b,9,10,10a-hexahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole

HRID 51047Notes

Reaction equation

HRID 51047 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:14]3=[C:15]([O:17][CH2:18][CH2:19][N:13]3[C@H:12]3[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][C@@H:11]23)[CH:16]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[C:14]3=[C:15]([O:17][CH2:18][CH2:19][N:13]3[C@H:12]3[CH2:20][CH2:21][N:22]=[CH:23][C@H:11]23)[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21302658HCID 21302658, compound

Product 1

HCID 69514318(6bR,10aS)-5-(2-chlorophenyl)-1,2,6b,9,10,10a-hexahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indoleYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl(6bR,10aS)-5-(2-chlorophenyl)-1,2,6b,9,10,10a-hexahydro[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole-8(7H)-carboxylate in CH2Cl2 (2.4 mL) was added TFA (0.6 mL) and the reaction mixture was stirred for 3 h. The reaction mixture was concentrated in vacuo, diluted with CH2Cl2 (100 mL), washed with NaHCO3 (100 mL) and brine (100 mL), dried over MgSO4 and concentrated in vacuo to afford the title compound (130 mg, 95%) as a light yellow oil. 1H NMR (CDCl3) δ1.78-1.99 (m, 2H), 2.11 (br-s, 1H), 2.76-2.95 (m, 4H), 3.09-3.20 (m, 2H), 2.32-2.39 (m, 1H), 2.41-2.46 (m, 1H), 4.44-4.52 (m, 2H), 6.76 (dd, 1H, J=1.5, 13.2 Hz), 7.19-7.36 (m, 4H), 7.42 (dd, 1H, J=1.4, 7.7 Hz) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with CH2Cl2 (100 mL)
  3. washwashed with NaHCO3 (100 mL) and brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f3eb2d30f5d4df398b26b3986944328
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

Loading…