Diisobutylaluminum hydride → 2-Tert-butoxycarbonylamino-4-oxo-butyric acid benzyl ester

HRID 480238Notes

Reaction equation

HRID 480238 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[CH:10]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:11][C:12](N(OC)C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH2:1]([O:8][C:9](=[O:26])[CH:10]([NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:11][CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 207010802-Tert-butoxycarbonylamino-n-methoxy-n-methyl succinamic acid benzyl ester

Product 1

HCID 143577952-Tert-butoxycarbonylamino-4-oxo-butyric acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2-tert-butoxycarbonylamino-N-methoxy-N-methyl succinamic acid benzyl ester (0.50 g, 1.36 mmol) in THF (5 mL) at −78° C. was added DIBAL-H (0.233 g, 1.67 mmol) dropwise. The mixture was stirred for 1.5 h and monitored by TLC. When completed the reaction was quenched with 5 mL of saturated solution of Rochell salt (KNaC4H4O6.4H2O) (potassium sodium tartrate) and extracted with EtOAc (2×10 mL). The organic layer was washed with H2O, brine, dried over Na2SO4, filtered and concentrated in vacuo to give the title compound in quantitative yield (0.40 g).

Workup

  1. customwas quenched with 5 mL of saturated solution of Rochell salt (KNaC4H4O6.4H2O) (potassium sodium tartrate)
  2. extractionextracted with EtOAc (2×10 mL)
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-358268208ef44d11b8d88b23073c9820
Source dataset
uspto-grants-2003_11
Patent number
US06649642B2

Reaction notes

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