HCID 67883980, compound → HCID 70123704, compound

HRID 846054Notes

Reaction equation

HRID 846054 reaction equation
[O:1]=[C:2]1[CH2:10][C@@H:9]2[C@@:4]3([C:11]4[N:12]([C:15](=[O:18])[CH2:16][CH:17]=4)[CH2:13][CH2:14][N:3]13)[CH2:5][CH2:6][CH2:7][CH2:8]2>O1CCCC1>[O:1]=[C:2]1[CH2:10][C@@H:9]2[C@@:4]3([C@H:11]4[CH2:17][CH2:16][C:15](=[O:18])[N:12]4[CH2:13][CH2:14][N:3]13)[CH2:5][CH2:6][CH2:7][CH2:8]2

Participants

3

Reactant 1

HCID 67883980HCID 67883980, compound

Product 1

HCID 70123704HCID 70123704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

985 mg (4 mmol) of (9bR*,13aR*)-2,7-dioxo-1,4,5,7,8,10,11,12,13,13a-decahydro-2H-pyrrolo[2',1':3,4]pyrazino[2,1-i]indole, dissolved in 40 ml of tetrahydrofuran, are hydrogenated with hydrogen in the presence of 98 mg of PtO2 at room temperature under normal pressure until the absorption of hydrogen ceases. The catalyst is filtered off and the filtrated is concentrated by evaporation in vacuo. The resulting oily crude product is crystallised from ethyl acetate. In this manner (9aR*,9bR*,13aR*)-2,7-dioxo-1,4,5,7,8,9,9a,10,11,12,13,13a-dodecahydro-2H-pyrrolo[2',1':3,4]pyrazino[2,1-i]-indole is obtained which melts at 135° to 136°. The mother liquor is concentrated by evaporation in vacuo and chromatographed on silica gel (0.040-0.063 mm) with trichloromethane and trichloromethane/methanol (99:1) as eluants. There is thus obtained (9aR*,9bS*,13aS*)-2,7-dioxo-1,4,5,7,8,9,9a,10,11,12,13,13a-dodecahydro-2H-pryrrolo[2',1':3,4]pyrazino[2,1-i]indole, which is stereoisomeric as regards the relative configuration of the 9a C-atom, in the form of an oil which is crystallised from ethyl acetate and then melts at 177°-179°.

Workup

  1. customare hydrogenated with hydrogen in the presence of 98 mg of PtO2 at room temperature under normal pressure until the absorption of hydrogen ceases
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrated is concentrated by evaporation in vacuo
  4. customThe resulting oily crude product is crystallised from ethyl acetate

Sources & evidence

ORD record
ord-0e82707181074c5785e5756cb31b9a86
Source dataset
uspto-grants-1992_08
Patent number
US05135930

Reaction notes

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