Trifluoroacetic acid → HCID 67884061, compound

HRID 846053Notes

Reaction equation

HRID 846053 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[O:12]=[C:13]1[CH2:21][C@@H:20]2[C@@:15]3([C:22]4[N:23]([CH:26]=[CH:27][CH:28]=4)[CH2:24][CH2:25][N:14]13)[CH2:16][CH2:17][CH2:18][CH2:19]2.FC(F)(F)C(O)=O>ClCCl>[O:12]=[C:13]1[CH2:21][C@@H:20]2[C@@:15]3([C@H:22]4[CH:28]=[CH:27][C:26](=[O:9])[N:23]4[CH2:24][CH2:25][N:14]13)[CH2:16][CH2:17][CH2:18][CH2:19]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 70297m-Chloroperbenzoic acidHCID 67883915HCID 67883915, compound

Product 1

HCID 67884061HCID 67884061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4.05 g (20 mmol) of m-chloroperbenzoic acid are added in portions at room temperature, with stirring, to a solution of 2.3 g (10 mmol) of (9bR*,13aR*)-2-oxo-1,4,5,10,11,12,13,13a-octahydro-2H-pyrrolo[2',1':3,4]pyrazino[2,1-i]indole in 50 ml of dichloromethane (the exothermic reaction is maintained at room temperature using an ice-bath). 2.28 g (20 mmol) of trifluoroacetic acid are then added dropwise to the reaction mixture which is then stirred for 16 hours at room temperature. The reaction mixture is diluted with 100 ml of dichloromethane and then washed in succession with sodium hydrogen sulfite solution (5%) and sodium hydrogen carbonate solution (5%). The organic phase is separated off, dried over sodium sulfate and concentrated by evaporation in vacuo. The crude product obtainable in that manner is chromatographed on 210 g of silica gel (0.040-0.063 mm) using trichloromethane as eluant. In this manner (9aR*,9bR*,13aR*)-2,7-dioxo-1,4,5,7,9a,10,11,12,13,13a-decahydro-2H-pyrrolo[2',1' :3,4]pyrazino[2,1-i]indole is obtained in the form of an oil, which is crystallised from dichloromethane/diethyl ether and melts at 159°-162°.

Workup

  1. customthe exothermic reaction
  2. washwashed in succession with sodium hydrogen sulfite solution (5%) and sodium hydrogen carbonate solution (5%)
  3. customThe organic phase is separated off
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation in vacuo
  6. customThe crude product obtainable in that manner is chromatographed on 210 g of silica gel (0.040-0.063 mm)

Sources & evidence

ORD record
ord-7caeeb6a2243476aa323fc5b2380a42d
Source dataset
uspto-grants-1992_08
Patent number
US05135930

Reaction notes

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