CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.C([O:19][C:20]([C@@H:22]1[CH2:27][C@H:26]2[C@H:24]([CH2:25]2)[N:23]1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=O)C.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[C:31]([O:30][C:28]([N:23]1[C@H:22]([CH2:20][OH:19])[CH2:27][C@H:26]2[C@@H:24]1[CH2:25]2)=[O:29])([CH3:34])([CH3:33])[CH3:32]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.
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