Beta-Alanine → 3-(Cyano-methoxycarbonyl-methylene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

HRID 1455556Notes

Reaction equation

HRID 1455556 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=O)[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][O:18][C:19](=[O:23])[CH2:20][C:21]#[N:22].N1CCCCC1.NCCC(O)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11](=[C:20]([C:21]#[N:22])[C:19]([O:18][CH3:17])=[O:23])[CH2:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 7747Methyl cyanoacetateHCID 8082PiperidineHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate

Product 1

HCID 684418533-(Cyano-methoxycarbonyl-methylene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2 g of 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester, 1.2 ml of cyano-acetic acid methyl ester, 130 μl of piperidine and 38 mg of β-alanine in 4 ml of DMF is stirred at 70° C. for 48 hours, the mixture obtained is diluted with EtAc, washed with H2O and brine, the organic layer obtained is dried, solvent is removed in vacuo and the residue obtained is subjected to chromatography on silica gel. 3-(cyano-methoxycarbonyl-methylene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester is obtained in the form of an oil. 13C-NMR: 174.13, 162.27, 153.68, 115.37, 107.45, 80.70, 53.92, 53.08, 28.81.

Workup

  1. customthe mixture obtained
  2. additionis diluted with EtAc
  3. washwashed with H2O and brine
  4. customthe organic layer obtained
  5. customis dried
  6. customsolvent is removed in vacuo
  7. customthe residue obtained

Sources & evidence

ORD record
ord-60bf677e69ed4d37b1d7321e5276a8bf
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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