Methyl iodide → tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate
Reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C@@H:9]([CH2:19][OH:20])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:26]>CN(C=O)C>[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[C@@H:9]([CH2:19][O:20][CH3:26])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A solution of tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate (9.32 g) in DMF (15 ml) was added to a stirred suspension of sodium hydride (60% dispersion) (1.37 g) in DMF 100 ml) at −10° C. Iodomethane (2.13 ml) was added and the reaction allowed to warm to 20° C. The reaction mixture was quenched carefully with water and evaporated to dryness. The crude material was partitioned between ethyl acetate (250 ml) and water (100 ml). The organic layer was washed with brine (100 ml), dried over Magnesium sulphate, filtered and evaporated to give tert-butyl (2R,4R) 4-(tert-butyl-dimethyl-silyl)oxy-2-(methoxymethyl)pyrrolidine-1-carboxylate (6.68 g) as a colourless oil. NMR Spectrum: (DMSOd6) 0.02 (6H, s); 0.83-0.84 (9H, s); 1.36 (9H, s); 1.78 (1H, d); 1.99 (1H, s); 2.99 (1H, d); 3.19 (3H, d); 3.23-3.48 (3H, m); 3.80 (1H, s); 4.33 (1H, s).
Workup
- customThe reaction mixture was quenched carefully with water
- customevaporated to dryness
- customThe crude material was partitioned between ethyl acetate (250 ml) and water (100 ml)
- washThe organic layer was washed with brine (100 ml)
- dry with materialdried over Magnesium sulphate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-926cfebca1c54243a01a8b13c6509e5f
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08017611B2
Reaction notes
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