cis-1-[4-[3-Methoxy-4-[(phenylmethyl)amino]-1-piperidinyl]-1-oxobutyl]pyrrolidine → cis-1-[4-(4-Amino-3-methoxy-1-piperidinyl)-1-oxobutyl]pyrrolidine
Reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:9]CC2C=CC=CC=2)[CH2:7][CH2:6][N:5]([CH2:17][CH2:18][CH2:19][C:20]([N:22]2[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[CH2:4]1.[H][H]>[Pd].CO>[NH2:9][C@H:8]1[CH2:7][CH2:6][N:5]([CH2:17][CH2:18][CH2:19][C:20]([N:22]2[CH2:23][CH2:24][CH2:25][CH2:26]2)=[O:21])[CH2:4][C@H:3]1[O:2][CH3:1]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 53 parts of cis-1-[4-[3-methoxy-4-[(phenylmethyl)amino]-1-piperidinyl]-1-oxobutyl]pyrrolidine and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 3 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 28.3 parts (71.4%) of cis-1-[4-(4-amino-3-methoxy-1-piperidinyl)-1-oxobutyl]pyrrolidine as a residue (int. 43).
Workup
- filtrationthe catalyst was filtered off
- customthe filtrate was evaporated
- customThe residue was purified by column chromatography over silica gel using
- additiona mixture of trichloromethane and methanol
- customThe pure fractions were collected
- customthe eluent was evaporated
Sources & evidence
- ORD record
- ord-9a95bfd74b6f409daf8865967cb6ee72
- Source dataset
- uspto-grants-1990_12
- Patent number
- US04975439
Reaction notes
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