N,N,N',N'-Tetramethylethylenediamine → Methyl 3-((tert-butoxycarbonyl)amino)furan-2-carboxylate
Reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:2]1.CN(CCN(C)C)C.C([Li])CCC.[C:27](=O)([O:30]C)[O:28][CH3:29]>C1COCC1>[CH3:29][O:28][C:27]([C:2]1[O:1][CH:5]=[CH:4][C:3]=1[NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:30]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of tert-butyl furan-3-ylcarbamate 32 (1.7 g, 1.0 eq) in THF (50 ml) at −30° C. was added TMEDA (1.75 ml, 1.3 eq) followed by 1.6M solution of n-butyllithium (8.4 ml, 2.25 eq, 1.6M in hexanes). Reaction mixture was allowed to warm up to 0° C. and stirred for 1 h, before being cooled back to −30° C. Dimethyl carbonate (2.4 ml, 3.0 eq) was quickly added, before the reaction mixture was allowed to warm up to room temperature for 1 hr. Reaction mixture was quenched with 2M HCl, followed by addition of saturated aq. NaCl. Mixture was extracted with ethyl acetate. The combined organic extracts were dried with Na2SO4 and concentrated. The crude reaction mixture was purified by flash chromatography to yield tert-butyl 2-(methoxycarbonyl)furan-3-ylcarbamate 33 (1.14 g, 51%): MS (Q1) 242 (M)+.
Workup
- customReaction mixture
- temperaturebefore being cooled back to −30° C
- temperatureto warm up to room temperature for 1 hr
- customReaction mixture
- customwas quenched with 2M HCl
- additionfollowed by addition of saturated aq. NaCl
- extractionMixture was extracted with ethyl acetate
- dry with materialThe combined organic extracts were dried with Na2SO4
- concentrationconcentrated
- customThe crude reaction mixture
- customwas purified by flash chromatography
Sources & evidence
- ORD record
- ord-60c6604aca7c48c6b46ec3476e7d08a6
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07846929B2
Reaction notes
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