Potassium Carbonate → potassium (S)-((4-(tert-butoxycarbonyl)-2-methylpiperazin-1-yl)methyl)trifluoroborate
Reaction equation
Br[CH2:2][B-:3]([F:6])([F:5])[F:4].[K+:7].[CH3:8][C@@H:9]1[NH:14][CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[C:18]([O:17][C:15]([N:11]1[CH2:12][CH2:13][N:14]([CH2:2][B-:3]([F:6])([F:5])[F:4])[C@@H:9]([CH3:8])[CH2:10]1)=[O:16])([CH3:21])([CH3:19])[CH3:20].[K+:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of potassium (bromomethyl)trifluoroborate (Aldrich, 1.20 g, 5.38 mmol) and (S)-tert-butyl 3-methylpiperazine-1-carboxylate (Aldrich, 1.131 g, 5.65 mmol) in THF (7.00 mL) was heated at 80° C. under nitrogen for 24 h. The mixture was allowed to cool to ambient temperature and was then concentrated in vacuo. The residue was re-dissolved in acetone (125 mL) and treated with K2CO3 (1 eq). The suspension was stirred for 30 min and then filtered through a short plug of Celite® (diatomaceous earth). The filter cake was washed with additional acetone, and the combined organic filtrates were concentrated to give the crude product as a colorless foam (1.51 g, 88%). The pure material was obtained as a beige powder by adding acetone-ether (2:1) to the foam and then slowly adding hexanes while sonicating the mixture. 19F-NMR (377 MHz, d6-acetone) δ −141.28.
Workup
- temperatureto cool to ambient temperature
- concentrationwas then concentrated in vacuo
- dissolutionThe residue was re-dissolved in acetone (125 mL)
- filtrationfiltered through a short plug of Celite® (diatomaceous earth)
- washThe filter cake was washed with additional acetone
- concentrationthe combined organic filtrates were concentrated
Sources & evidence
- ORD record
- ord-fad01d565fb0436d93bd2e088dec1910
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362241B2
Reaction notes
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