p-Toluenesulfonate → (S)-2-Methyl-[1,4]bipiperidinyl

HRID 1512047Notes

Reaction equation

HRID 1512047 reaction equation
Cl.Cl.C[C@H]1CCCN1[C@@H]1CCNC1.[C:14]([C@:21]1(C)[CH2:26][CH2:25][CH2:24][CH2:23][N:22]1[CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)(OC(C)(C)C)=O.S(C1C=CC(C)=CC=1)([O-])(=O)=O>>[CH3:14][C@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][N:22]1[CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1

Participants

4

Reactant 3

HCID 85570p-ToluenesulfonateHCID 67423613(2S,3'R)-2-Methyl-[1,3']bipyrrolidinyl dihydrochlorideHCID 67423644BOC-(S)-2-Methyl-[1,4]bipiperidinyl

Product 1

HCID 28213026(S)-2-Methyl-[1,4]bipiperidinylYield 94%

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-(S)-2-Methyl-[1,4′]bipiperidinyl which was synthesized by condensation of corresponding tosylate with (S)-(−)-2-methylpiperindine to get 1.37 g (94% yield) of the title product as a clear oil.

Sources & evidence

ORD record
ord-ca5c22ced8ae4f38bfb622a692fc23be
Source dataset
uspto-grants-2012_07
Patent number
US08217052B2

Reaction notes

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