Hydrochloric Acid → 2H-benzo-furo[2,3-a]quinolizine-2-carbonitrile
Reaction equation
Cl.Cl.C([CH:5]1[C@@H:14]2[N:9]([CH2:10][CH2:11][C:12]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[O:15][C:13]=32)[CH2:8][CH2:7][C@H:6]1NCCCS(N)(=O)=O)#N.[C:30](N1C=CN=C1)([N:32]1C=CN=C1)=O.Cl>>[CH:5]1[CH:6]([C:30]#[N:32])[CH:7]=[CH:8][N:9]2[C:14]=1[C:13]1[O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:12]=1[CH:11]=[CH:10]2Participants
Procedure
in the second step (2R,12bS)-[2-[(cyano-1,3,4,6,7,12b-hexahydrobenzofuro-[2,3-a]quinolizine-2-yl)-amino]-ethyl]methanesulfonamide dihydrochloride is contacted with 1,1′-carbonyldiimidazole in the presence of a hydrogen chloride acceptor in an organic solvent to obtain (2R,12bS)-1,3,4,6,7,12b-hexahydro-[2,3-methylsulfonyl)-2-oxo-1-imidazolidinyl]-2H-benzo-furo[2,3-a]quinolizine-2-carbonitrile, and in the third step (2R,12bS)-1,3,4,6,7,12b-hexahydro-[2,3-methylsulfonyl)-2-oxo-1-imidazolidinyl]-2H-benzofuro[2,3-a]quinolizine-2-carbonitrile is contacted with hydrogen in the presence of Raney nickel catalyst and sodium methoxide or potassium tert-butoxide in methanol solvent to yield N-(2-((2R,12bS)-2′-oxo-1,3,4,6,7,12b-hexa-hydrospiro[benzo-furo[2,3-a]quinolizine-2,4′-imidazolidine]-3′-yl)ethyl)-methanesulfonamide.
Sources & evidence
- ORD record
- ord-188192aaf2c4403bba55139aeac85d51
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409919B2
Reaction notes
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