1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine → tert-Butyl 3-(cyanomethyl)azetidine-1-carboxylate

HRID 1506255Notes

Reaction equation

HRID 1506255 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1)#[N:2]>CO.O1CCOCC1.[C].[Pd]>[C:1]([CH2:3][CH:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1)#[N:2]

Participants

5

Reactant 1

HCID 457892161-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine

Product 1

HCID 53234188tert-Butyl 3-(cyanomethyl)azetidine-1-carboxylateYield 79%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 3-(cyanomethylene)azetidine-1-carboxylate (823 mg, 4.24 mmol) in a mixture of methanol (20 mL) and 1,4-dioxane (10 mL) was stirred with 5% palladium-carbon (129 mg) for one day under a hydrogen atmosphere. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)) to give the title compound as a colorless oil (657 mg, yield 79%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-4a860eecf3d947a890d89964001946ec
Source dataset
uspto-grants-2015_12
Patent number
US09216999B2

Reaction notes

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