Methanol → tert-butyl (1R*,4S*,6R*)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate
Reaction equation
[N+](C1C=CC(C([O:12][CH2:13][C@@H:14]2[CH2:20][C@@H:19]3[C@@H:17]([CH2:18]3)[CH2:16][N:15]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O)=CC=1)([O-])=O.O1CCCC1.CO.O.[OH-].[Li+]>[Cl-].[Na+].O.O>[OH:12][CH2:13][C@@H:14]1[CH2:20][C@@H:19]2[C@@H:17]([CH2:18]2)[CH2:16][N:15]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a mixture of tert-butyl (1R*,4S*,6R*)-4-({[(4-nitrophenyl)carbonyl]oxy}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate (8.2 g) produced above, tetrahydrofuran (70 mL), methanol (70 mL) and water (35 mL) was added lithium hydroxide monohydrate (2.7 g). The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with brine, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (3.5 g).
Workup
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous sodium sulfate
- filtrationInsoluble material was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)
Sources & evidence
- ORD record
- ord-e2100ea2ab414ca6bc6da55aa3085012
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722660B2
Reaction notes
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