Methanol → (1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-hydroxy-6-aza-bicyclo[3.2.1]octane-6-carboxylate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:18][CH2:17][C@@H:16]2[CH2:19][C@H:13]1[C:14](=[O:27])[N:15]2[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.CO.O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:18][CH2:17][C@@H:16]2[CH2:19][C@H:13]1[CH:14]([OH:27])[N:15]2[C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
Procedure
A solution of (1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (2.62 g, 7.0 mmol) in dichloromethane (50 mL) was stirred on an ice bath and treated dropwise with diisobutylaluminum hydride (1.0 M in tetrahydrofuran, 21 mL, 21 mmol) over ca. 10 min. The solution was stirred on ice for 4 h 5 min, then was treated dropwise over 10 min with methanol (1.75 mL). The mixture was stirred on ice for 10 min, then was treated with water (2.75 mL) over ca. 1 min. The mixture was stirred at rt for 35 min, then was filtered and the gelatinous solid was triturated 3× with dichloromethane and filtered. The combined filtrates were combined and concentrated under vacuum to provide (1R,2S,5R)-tert-butyl 2-(benzyloxycarbonylamino)-7-hydroxy-6-aza-bicyclo[3.2.1]octane-6-carboxylate as a sticky semicrystalline solid (2.41 g). MS found: (M+H—H2O)+=359.3.
Workup
- stirringThe mixture was stirred on ice for 10 min
- stirringThe mixture was stirred at rt for 35 min
- filtrationwas filtered
- customthe gelatinous solid was triturated 3× with dichloromethane
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-cb4a0fbfc29f43b6b27d5cc6bf07bf8a
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378409B2
Reaction notes
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