Diisopropylamine → HCID 57425767, compound

HRID 1441240Notes

Reaction equation

HRID 1441240 reaction equation
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[C:13]([O:17][C:18]([N:20]1[CH2:23][CH:22]([C:24]#[N:25])[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].BrCC1CC1>C1COCC1>[C:24]([C:22]1([CH2:8][CH:9]2[CH2:11][CH2:10]2)[CH2:23][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:19])[CH2:21]1)#[N:25]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 81503BromomethylcyclopropaneHCID 106312831-Boc-3-cyanoazetidineHCID 178418339Butyllithium

Product 1

HCID 57425767HCID 57425767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (3.33 g 4.64 ml; 32.92 mmol) in THF (60 ml) at 0° C. was added n-butyllithium (2.5M in hexanes; 13.17 ml; 32.92 mmol). The solution was stirred for 30 minutes then cooled to −78° C. A solution of 3-cyanoazetidine-1-carboxylic acid tert-butyl ester (5 g; 27.43 mmol) in THF (40 ml) was added and the solution stirred for 1 hour. (Bromomethyl)cyclopropane (4.81 g 3.42 ml; 35.67 mmol) was then added dropwise with stirring and the solution stirred for 30 minutes at −78° C., then allowed to warm to ambient temperature, and stirred for 3 hours. The reaction was cooled in an ice bath and quenched with saturated aqueous ammonium chloride. The solvent was evaporated and the residue was partitioned between EtOAc (300 ml) and water (100 ml). The organic phase was separated, dried over MgSO4, filtered and evaporated to give an orange oil. The crude product was passed through a silica gel plug eluted with 15% EtOAc DCM to give the product as a pale yellow oil. (5.25 g)

Workup

  1. stirringthe solution stirred for 1 hour
  2. stirringwith stirring
  3. stirringthe solution stirred for 30 minutes at −78° C.
  4. temperatureto warm to ambient temperature
  5. stirringstirred for 3 hours
  6. temperatureThe reaction was cooled in an ice bath
  7. customquenched with saturated aqueous ammonium chloride
  8. customThe solvent was evaporated
  9. customthe residue was partitioned between EtOAc (300 ml) and water (100 ml)
  10. customThe organic phase was separated
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. customevaporated
  14. customto give an orange oil
  15. washeluted with 15% EtOAc DCM

Sources & evidence

ORD record
ord-b7c6d880a1a54093a442af04cc2a8623
Source dataset
uspto-grants-2010_02
Patent number
US07655644B2

Reaction notes

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