Ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate → Ethyl 3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane-10-carboxylate

HRID 5406

Reaction equation

HRID 5406 reaction equation
[C:1]([O:5][C:6]([CH:8]=[C:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:11][C:10]1=[O:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[NH:11][C:10]1=[O:24])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 54383214Ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate

Product 1

HCID 19930811Ethyl 3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane-10-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate (2.85 g, 8.4 mmol) is dissolved in ethyl acetate (75 mL). 10% Pd/C (2.0 g) is added, and the reaction is stirred under an atmosphere of hydrogen for 4.5 hours. The reaction is filtered through Celite, and the solvent is removed. The crude product is purified by silica gel chromatography (20% ethyl acetate/hexane) to give separately the two diastereomers of ethyl 3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane-10-carboxylate.

Workup

  1. filtrationThe reaction is filtered through Celite
  2. customthe solvent is removed
  3. customThe crude product is purified by silica gel chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-17a0cf59456c4baa92e9560f5124e23f
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Linked notes

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