Sodium Hydroxide → Di-tert-butyl dicarbonate

HRID 611053Notes

Reaction equation

HRID 611053 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][N:8]2[C:12](=[O:13])C3=CC=CC=C3C2=O)=[CH:2]1.O.NN.[OH-].[Na+].[C:24]([O:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C(O)C.ClCCl>[C:27]([O:26][C:12]([NH:8][CH2:7][CH2:6][C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)=[O:13])([CH3:30])([CH3:29])[CH3:28].[C:32]([O:31][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([O:34][C:35]([CH3:37])([CH3:38])[CH3:36])=[O:33]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 90495Di-tert-butyl dicarbonateHCID 19600279HCID 19600279, compound

Product 2

HCID 90495Di-tert-butyl dicarbonateHCID 11469899Carbamic acid, [2-(3-furanyl)ethyl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 19.020 g (78.839 mmol) of N-[2-(3-furyl)ethyl]phthalimide and 5.74 ml (118 mmol) of hydrazine monohydrate in 200 ml of ethanol was refluxed for 1 hour. After cooling to room temperature, the reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude 2-(3-furyl)ethylamine was dissolved in 150 ml of dichloromethane; a solution of 22.4 g (102 mmol) of di-tert-butyl dicarbonate in 50 ml of dichloromethane was added dropwise at room temperature, followed by stirring for 0.5 hours. The solvent was distilled off under reduced pressure; the resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 6/1) to yield N-tert-butoxycarbonyl-2-(3-furyl)ethylamine as a mixture with di-tert-butyl dicarbonate.

Workup

  1. extractionextracted with dichloromethane 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe resulting crude 2-(3-furyl)ethylamine was dissolved in 150 ml of dichloromethane
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1 to 6/1)

Sources & evidence

ORD record
ord-9503bac4357e43ff9c13024fd37664d9
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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