1,5-Diazabicyclo(4.3.0)non-5-ene → 2,3,5,6,7,7a-Hexahydro-1H-pyrrolo[3,4-b]pyridine

HRID 1780770Notes

Reaction equation

HRID 1780770 reaction equation
N1CCC[C@H]1C(O)=O.[N:9]12[CH2:19][CH2:18][CH2:17][N:16]=[C:15]1[CH2:14][CH2:13]CC[CH2:10]2.N12CCCC1=NCCC2.N=C=N>C(N(CC)CC)C.C(Cl)(Cl)Cl.C(#N)C.CS(C)=O.CN(C)C=O>[CH:17]12[CH2:10][NH:9][CH2:19][C:18]1=[CH:13][CH2:14][CH2:15][NH:16]2

Participants

10

Reactant 4

HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 145742L-ProlineHCID 160435Carbodiimide

Product 1

HCID 152370792,3,5,6,7,7a-Hexahydro-1H-pyrrolo[3,4-b]pyridine

Reagents, catalysts & solvents 5

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Compound (II) is reacted with N-tosyl-L-prolyl chloride in an organic solvent such as methylene chloride or chloroform or in a mixture of water and the said organic solvents in the presence of an organic base such as triethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) or an inorganic base such as sodium bicarbonate or sodium carbonate at -20° C. to 30° C. to give Compound (a). Compound (a) may also be prepared by reacting Compound (II) with N-protected L-proline in a solvent such as N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO), acetonitrile or chloroform in the presence of an organic or inorganic base such as triethylamine, DBU or DBN and dicyclokexyl carbodiimide. Compound (a) is subjected to column chromatography and acid-catalized hydrolysis to obtain Compound (IIa) and Compound (IIa').

Workup

  1. customto obtain Compound (IIa) and Compound (IIa')

Sources & evidence

ORD record
ord-9f7703e48cbb46a1bf4734a16320244e
Source dataset
uspto-grants-1997_05
Patent number
US05631266

Reaction notes

Loading…