HCID 67884061, compound → HCID 70123704, compound

HRID 1590581Notes

Reaction equation

HRID 1590581 reaction equation
[O:1]=[C:2]1[CH2:10][C@@H:9]2[C@@:4]3([C@H:11]4[CH:17]=[CH:16][C:15](=[O:18])[N:12]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 67884061HCID 67884061, compound

Product 1

HCID 70123704HCID 70123704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

700 mg (2.8 mmol) of (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, dissolved in 30 ml of tetrahydrofuran, are hydrogenated with hydrogen in the presence of 70 mg of PtO2 at room temperature under normal pressure until the absorption of hydrogen ceases. The catalyst is filtered off and the filtrate is concentrated by evaporation in vacuo. The resulting oil 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 of formula ##STR6## is obtained, that is to say the compound of formula I in which R1, R2, R3, R4, R5, R6 and R7 are each a hydrogen atom, m is 2, n is 1 and the chiral C-atoms 9a, 9b and 13a have the above relative configuration (each R*) (melting range: 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-pyrrolo[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 70 mg of PtO2 at room temperature under normal pressure until the absorption of hydrogen ceases
  2. filtrationThe catalyst is filtered off
  3. concentrationthe filtrate is concentrated by evaporation in vacuo
  4. customThe resulting oil is crystallised from ethyl acetate

Sources & evidence

ORD record
ord-03fa2c6b7497422887c419bde4025feb
Source dataset
uspto-grants-1993_04
Patent number
US05204342

Reaction notes

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