p-Toluenesulfonate → 4-((S)-2-Methyl-pyrrolidin-1-yl)piperidine

HRID 1512046Notes

Reaction equation

HRID 1512046 reaction equation
Cl.Cl.C[C@H]1CCCN1[C@@H]1CCNC1.C([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[CH2:31][CH2:30][CH2:29][C@@H:28]2[CH3:32])[CH2:23][CH2:22]1)(OC(C)(C)C)=O.S(C1C=CC(C)=CC=1)([O-])(=O)=O.C[C@H]1CCCN1>>[CH3:32][C@H:28]1[CH2:29][CH2:30][CH2:31][N:27]1[CH:24]1[CH2:25][CH2:26][NH:21][CH2:22][CH2:23]1

Participants

5

Reactant 4

HCID 85570p-ToluenesulfonateHCID 6999702(2S)-2-methylpyrrolidineHCID 58468064BOC-4-((S)-2-Methyl-pyrrolidin-1-yl)piperidineHCID 67423613(2S,3'R)-2-Methyl-[1,3']bipyrrolidinyl dihydrochloride

Product 1

HCID 584680514-((S)-2-Methyl-pyrrolidin-1-yl)piperidineYield 95%

Procedure

The title compound was prepared in a manner substantially the same as intermediate (2S,3′R)-2-Methyl-[1,3′]bipyrrolidinyl dihydrochloride by acid hydrolysis of BOC-4-((S)-2-Methyl-pyrrolidin-1-yl)piperidine which was synthesized by condensation of tosylate with (S)-(−)-2-methylpyrrolidine to get 1.28 g (95% yield) of the title product as a clear oil.

Sources & evidence

ORD record
ord-687b357bbdf44345b7ff9eeadb6268de
Source dataset
uspto-grants-2012_07
Patent number
US08217052B2

Reaction notes

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