Divinylbenzene-styrene → 1-Piperidinecarboxylicacid,4-hydroxy-2-methyl-,1,1-dimethylethylester,(2S,4S)-(9CI)

HRID 1109758Notes

Reaction equation

HRID 1109758 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C@H:11]([O:14]C2CCCCO2)[CH2:10][C@@H:9]1[CH3:21])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C=CC1C=CC=CC=1.C(C1C=CC=CC=1C=C)=C>CO>[C:1]([N:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10][C@@H:9]1[CH3:21])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 174664Divinylbenzene-styreneHCID 67823597HCID 67823597, compound

Product 1

HCID 450974401-Piperidinecarboxylicacid,4-hydroxy-2-methyl-,1,1-dimethylethylester,(2S,4S)-(9CI)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 14.6 g (0.04876 mol) of cis-N-BOC-2-methyl-4-[(tetrahydropyran-2-yl)oxy]piperidine in 120 ml of methanol is treated with 20 g of cationic exchanger Dowex® 50 WX8 (H+ form; 50-100 mesh (50 mesh corresponds to a granular size of c. 300 μm, 100 mesh to c. 150 μm); cationic exchanger based on a styrene/divinylbenzene polymer containing sulfonyl groups; registered trademark of Dow Chemicals Co., USA)), and the mixture is stirred for 22 hours at room temperature. After filtration, washing the ion exchanger with methanol and concentrating the filtrate under vacuum, the title compound is obtained in the form of a viscous oil, Rf =0.16 (silica gel/ethyl acetate:hexane (1:2)).

Workup

  1. additioncontaining sulfonyl groups
  2. filtrationAfter filtration
  3. washwashing the ion exchanger with methanol
  4. concentrationconcentrating the filtrate under vacuum

Sources & evidence

ORD record
ord-b7de7f78a9d24f4f8d50fb29c93f5b05
Source dataset
uspto-grants-1994_06
Patent number
US05322852

Reaction notes

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