m-Chloroperbenzoic acid → HCID 67883980, compound

HRID 846056Notes

Reaction equation

HRID 846056 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>ClCCl>[O:12]=[C:13]1[CH2:21][C@@H:20]2[C@@:15]3([C:22]4[N:23]([C:26](=[O:9])[CH2:27][CH:28]=4)[CH2:24][CH2:25][N:14]13)[CH2:16][CH2:17][CH2:18][CH2:19]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67883915HCID 67883915, compound

Product 1

HCID 67883980HCID 67883980, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3.04 g (15 mmol) of m-chloroperbenzoic acid in 30 ml of dichloromethane is added dropwise over a period of 45 minutes at -15°, with stirring, to a solution of 2.3 g (10 mmol) of (+)-(9bR*,13aR*)-2oxo-1,4,5,10,11,12,13,13a-octahydro-2H-pyrrolo[2',1':3,4]pyrazino[2,1-i]indole in 30 ml of dichloromethane. The reaction mixture is then stirred for 4 hours at -15°, then diluted with 100 ml of dichloromethane and washed in succession, while ice-cold, 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 (+)-(9bR*,13aR*)-2,7-dioxo-1,4,5,7,8,10,11,12,13,13a-decahydro-2H-pyrrolo[2',1':3,4]pyra zino[2,1-i]indole is obtained in the form of a foam, which can be further reacted without being further purified.

Workup

  1. washwashed in succession, while ice-cold, with sodium hydrogen sulfite solution (5%) and sodium hydrogen carbonate solution (5%)
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-115a2bed2c054f2fb26b77a6afbbc2d5
Source dataset
uspto-grants-1992_08
Patent number
US05135930

Reaction notes

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