Ethyl Acetate → 4-(2-Methoxy-ethyl)-2-oxo-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

HRID 420648Notes

Reaction equation

HRID 420648 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][O:21][CH3:22])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CC[O:25]C(C)=O>O>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][O:21][CH3:22])[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[C:10](=[O:25])[CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8857Ethyl Acetate2×HCID 582872614-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 584784134-(2-Methoxy-ethyl)-2-oxo-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

4-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (13 g) in AcOEt (300 ml) was added at RT under an argon atmosphere to a vigorously stirred solution of RuCl3×H2O (1.71 g) and NaIO4 (44.078 g) in water (300 ml). This mixture was vigorously stirred 30 minutes at RT. Then water and AcOEt were added and the layers were separated. The organic layer was washed with water and brine, dried over magnesium sulphate and concentrated to give the crude product as brown oil (8.78 g) which was used in next reaction step without further purification. MS (ESI): 352.17 (M+Na)+ and 230.13 [(M-C5H8O2)H+]

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eafe9d8af615441a8a571eb54cfe8423
Source dataset
uspto-grants-2012_01
Patent number
US08097634B2

Reaction notes

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