反应详情

At −78° C. a solution of DIBAL in toluene (1.0 M, 47 mmol, 47 mL) is added dropwise to a solution of (1S,3S,5S)-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester (21.4 mmol) in THF (60 mL). After 50 min the mixture is allowed to reach RT, stirred for additional 50 min and poured into a mixture of aqueous NaOH solution (1.0 M) and ice. EtOAc is added, the layers are separated and the aqueous layer is extracted with EtOAc (3×70 mL). The combined organic layers are washed with aqueous NaOH solution (1.0 M) and brine, dried over Na2SO4 and concentrated in vacuo to give the desired alcohol as a colourless oil. LC-MS (acidic): tR=0.79 min; [M+H]+=214.3.

1. customto reach RT
2. customthe layers are separated
3. extractionthe aqueous layer is extracted with EtOAc (3×70 mL)
4. washThe combined organic layers are washed with aqueous NaOH solution (1.0 M) and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated in vacuo