Trifluoroacetic acid → HCID 11356636, compound

HRID 1266127Notes

Reaction equation

HRID 1266127 reaction equation
[CH:1]1[C:10]2[CH:11]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13][CH:12]3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1[C:10]2[CH:11]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13][CH:12]3[N:8]3[C:9]=2[C:4]([CH2:5][CH2:6][CH2:7]3)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86593177HCID 86593177, compound

Product 1

HCID 11356636HCID 11356636, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of tert-butyl (±)-5,6,8,9,10,11,12,12a-octahydro-4H,7aH-azepino[4′,5′:4,5]pyrrolo[3,2,1-ij]quinoline-10-carboxylate in CH2Cl2 (2.4 mL) was added TFA (0.6 mL). This was stirred at 20° C. for 3 h. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with saturated NaHCO3 (50 mL) and brine (50 mL), dried over MgSO4 and concentrated in vacuo to afford the title compound as a yellow oil (87 mg, 59%). 1H NMR (CDCl3, 300 MHz) δ1.77-2.13 (m, 7H), 2.56-2.79 (m, 5H), 2.83-2.93 (m, 1H), 3.00-3.16 (m, 2H), 3.33-3.41 (td, 1H, J=3.7, 9.2 Hz), 3.60 (td, 1H, J=4.4, 9.1 Hz), 6.50 (t, 1H, J=7.3 Hz), 6.76 (t, 2H, 8.0 Hz) ppm.

Workup

  1. washwashed with saturated NaHCO3 (50 mL) and brine (50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a75e096546e2479886d6e26f463d03b5
Source dataset
uspto-grants-2003_04
Patent number
US06548493B1

Reaction notes

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