Sodium Iodide → tert-Butyl benzyloxy(4-cyanobutyl)carbamate

HRID 2426251Notes

Reaction equation

HRID 2426251 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].[H-].[Na+].Cl[CH:22]([CH3:27])[CH2:23][CH2:24][C:25]#[N:26]>CN(C)C=O>[CH2:1]([O:8][N:9]([CH2:27][CH2:22][CH2:23][CH2:24][C:25]#[N:26])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 736159Tert-butyl N-(benzyloxy)carbamateHCID 232662284-chloropentanenitrile

Product 1

HCID 10685938tert-Butyl benzyloxy(4-cyanobutyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of tert-butyl benzyloxycarbamate in anhydrous dimethylformamide were added 5 mol % of sodium iodide and portionwise 1.36 eq. of sodium hydride (60% dispersion in mineral oil). The mixture was stirred at room temperature for 15 min. before 1.05 eq. of 4-chlorovaleronitrile were added. The mixture was heated to 85° C. and stirred for 3.5 h. After cooling to room temperature the mixture was quenched with water and extracted with diethyl ether. The combined organic phases were concentrated and washed with half saturated aq. sodium thiosulfate, water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated under reduced pressure. The oily residue was washed with petroleum ether and dried under high vacuum to yield Tert-butyl benzyloxy(4-cyanobutyl)carbamate as a light yellow oil.

Workup

  1. additionwere added
  2. temperatureAfter cooling to room temperature the mixture
  3. customwas quenched with water
  4. extractionextracted with diethyl ether
  5. concentrationThe combined organic phases were concentrated
  6. washwashed with half saturated aq. sodium thiosulfate, water and brine
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. washThe oily residue was washed with petroleum ether
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-7353cc4a02e240809d71eedd34a289cb
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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