Carbon Dioxide → Lithium 5-(tert-butoxycarbonyl)-4,5,6,7-tetrahydrothiazolo[5,4-C]pyridine-2-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15](Br)[S:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li:18]CCCC.[C:23](=[O:25])=[O:24]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([C:23]([O-:25])=[O:24])[S:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Dissolved 2-bromo-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester (650 mg, 2.036) in dry THF and the mixture was cooled to −78° C. To this was added n-BuLi in a dropwise fashion. The mixture was stirred for 30 min at 4° C. and then was re-cooled to −78° C. and solid CO2 was added in one portion. The mixture was warmed to room temperature, stirred for 1 h and was concentrated to give 132.5 mg of lithium 5-tert-butoxycarbonyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine-2-carboxylate.
Workup
- temperaturewas re-cooled to −78° C.
- temperatureThe mixture was warmed to room temperature
- stirringstirred for 1 h
- concentrationwas concentrated
Sources & evidence
- ORD record
- ord-ab2fed1b6b794f69985ab55df445a39e
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093266B2
Reaction notes
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