HCID 10854740, compound → tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(propan-2-yl)pyrrolidine-1-carboxylate
Reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:21]([CH3:23])=[CH2:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Ni]>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH:21]([CH3:23])[CH3:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate (90 g) dissolved in methanol (250 mL) was added Raney Nickel (24 g). The reaction mixture was stirred under hydrogen (40 atm) at 60° C. for 3 hours. The mixture was filtered and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with brine (2×50 mL), dried over magnesium sulfate, filtered and concentrated to give tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(propan-2-yl)pyrrolidine-1-carboxylate. The residue was used directly without further purification.
Workup
- filtrationThe mixture was filtered
- concentrationconcentrated under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate
- washwashed with brine (2×50 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-42e043cae6344bf1975504d4c025e8e1
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846657B2
Reaction notes
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