Diisopropylamine → HCID 59420820, compound

HRID 499082Notes

Reaction equation

HRID 499082 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[C:14]#[CH:15].[O:20]=[C:21]1[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]1>C1COCC1>[CH2:18]([O:17][C:13]([C:14]#[C:15][C:21]1([OH:20])[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:24]1)=[O:16])[CH3:19]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 12182Ethyl propiolateHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 59420820HCID 59420820, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

n-butyl lithium (1.17 mmol, 0.47 ml, 2.5 M) was added dropwise to a solution of diisopropylamine (130 mg, 1.29 mmol, 0.18 ml) in THF (8 ml) at −78° C. The solution was warmed to 0° C., stirred for 15 mins, and cooled back to −78° C. Ethyl propiolate (126 mg, 1.29 mmol, 0.13 ml) was added dropwise and the solution stirred for 1 hr at −78° C. A solution of tert-butyl 3-oxoazetidine-1-carboxylate (200 mg, 1.17 mmol) in THF (2 ml) was added dropwise, stirring continued for 30 mins, and the solution warmed to 0° C. and stirred for a further 15 mins. The reaction was quenched with Sat NH4Cl (20 ml) and extracted into ethyl acetate (20 ml), dried (Na2SO4), and concentrated to give a brown oil. The oil was purified by flash column chromatography eluting with 30% ethylacetate/hexanes to give the title compound as a colorless oil 0.20 g, 64%. 1H NMR (CDCl3, 400 MHz) 1.33 (3H, t), 1.48 (9H, s), 2.92 (1H, s), 4.04 (2H, d), 4.22-4.31 (4H, m).

Workup

  1. temperaturecooled back to −78° C
  2. stirringthe solution stirred for 1 hr at −78° C
  3. stirringstirring
  4. waitcontinued for 30 mins
  5. temperaturethe solution warmed to 0° C.
  6. stirringstirred for a further 15 mins
  7. customThe reaction was quenched with Sat NH4Cl (20 ml)
  8. extractionextracted into ethyl acetate (20 ml)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customto give a brown oil
  12. customThe oil was purified by flash column chromatography
  13. washeluting with 30% ethylacetate/hexanes

Sources & evidence

ORD record
ord-7dbdc8d10e164b05a6e91d8259677e15
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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