Acetaldehyde → HCID 86713344, compound

HRID 928024Notes

Reaction equation

HRID 928024 reaction equation
[CH:1](=O)[CH3:2].[C:4]([O:8][C:9]([NH:11][CH:12]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]1[CH2:16][NH:15][CH2:14]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(O)C.[Pd]>[C:21]([O:20][C:18]([NH:17][CH:12]([NH:11][C:9]([O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:10])[CH:13]1[CH2:14][N:15]([CH2:1][CH3:2])[CH2:16]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 177AcetaldehydeHCID 86713345HCID 86713345, compound2×

Product 1

HCID 86713344HCID 86713344, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of acetaldehyde (1.5 g) and 3-[bis-(tert-butoxycarbonyl-amino)methyl]azetidine (Intermediate 151, 1.0 g) in ethanol (20 mL) was stirred at room temperature for 30 minutes and then 10% palladium on carbon (0.3 g) was added. The mixture was stirred under an atmosphere of hydrogen overnight. The solid was filtered off and the filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM (10%) to give 3-[bis-(tert-butoxycarbonylamino)methyl]-1-ethylazetidine (0.83 g) as a colourless liquid, which was used without further characterization.

Workup

  1. stirringThe mixture was stirred under an atmosphere of hydrogen overnight
  2. filtrationThe solid was filtered off
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by chromatography on silica
  5. washeluting with a mixture of methanol and DCM (10%)

Sources & evidence

ORD record
ord-50464cc87fd54da18e854e203b748b5f
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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