HCID 11861387, compound → Brucine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C@@:9]34[C@H:17]5[N:18]([C:19]([CH2:21][C@@H:22]6[O:23][CH2:24][CH:25]=[C:26]7[CH2:27][NH+:12]([C@H:13]3[CH2:14][C@@H:15]7[C@H:16]56)[CH2:11][CH2:10]4)=[O:20])[C:6]2=[CH:5][C:4]=1[O:28][CH3:29]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C@@:9]34[C@@H:13]5[CH2:14][C@H:15]6[C:26]([CH2:27][N:12]5[CH2:11][CH2:10]3)=[CH:25][CH2:24][O:23][C@H:22]3[CH2:21][C:19](=[O:20])[N:18]([C@H:17]4[C@@H:16]63)[C:6]2=[CH:5][C:4]=1[O:28][CH3:29]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To 2.3 liters acetonitrile was added 99.6 g (0.342 mol) of title product of the preceding Example and 147.0 g (0.342 mol) brucine dihydrate. The mixture was brought to reflux to effect almost complete solution of the reagents and slightly hazy particulate matter was removed by filtration of the hot solution. The filtrate was allowed to cool to 23° C. and after 20 hours, 96.5 g of white solid; m.p. 184°-187° C., [alpha]D25 =+11° (CH3OH, C=1) was collected by filtration. The mother liquors were set aside for recovery of the 2S,4S enantiomer and racemate and the entire batch of white solid was taken up in 1.5 liters acetonitrile at reflux to give a clear solution. The volume was reduced to 1.2 liters by boiling off acetonitrile, the solution was allowed to cool to 23° C. and after 20 hours partially purified title product recovered by filtration, 65 g of white crystals; m.p. 191°-195° C.; [alpha]D25 =+30° (CH3OH, C=1). This latter material was dissolved in 1.4 liters acetonitrile at reflux, the solution was allowed to cool to 23° C. and after 20 hours there was isolated by filtration 52.7 g of purified title product, white crystals; m.p. 193°-197° C.; [alpha]D25 =+36° (CH3OH, C=1). The absolute 2R,4Rstereochemistry of this compound was shown by X-ray crystallographic analysis.
Sources & evidence
- ORD record
- ord-c12ff3107f7c4250925eb1800b2df586
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04853410
Reaction notes
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