Triethylamine → HCID 10854740, compound
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](O)([CH3:23])[CH3:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[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])([CH3:2])[CH3:3]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-hydroxypropan-2-yl)pyrrolidine-1-carboxylate (98 g) dissolved in toluene (900 mL) at −78° C. was added triethylamine (310 mL). The mixture was stirred at −78° C. for 10 minutes, and then thionyl chloride (60 mL) in toluene (100 mL) was added dropwise over 1.5 hours. The mixture was stirred at −78° C. for 2 hours and then quenched with saturated ammonium chloride. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to give tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(prop-1-en-2-yl)pyrrolidine-1-carboxylate. The residue was used directly without further purification.
Workup
- stirringThe mixture was stirred at −78° C. for 2 hours
- customquenched with saturated ammonium chloride
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe organic layer was washed with saturated aqueous sodium bicarbonate and brine
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fff710c4ec6442ef8c9bb5109e1c603f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846657B2
Reaction notes
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