tert-Butyldimethylsilyl chloride → N-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)azetidin-2-one
Reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:9]([O:12][CH2:13][CH2:14][CH:15]1[NH:18][C:17](=[O:19])[CH2:16]1)(=[O:11])[CH3:10]>CCN(CC)CC>[Si:1]([N:18]1[CH:15]([CH2:14][CH2:13][O:12][C:9](=[O:11])[CH3:10])[CH2:16][C:17]1=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
Triethylauine (Et3N) (2.96 ml, 21.2 mmol) and t-butyldimethylsilyl chloride (3.059 g, 20.3 mmol) are added to an ice-cold stirring solution of 4-(2-acetoxyethyl)-azetidin-2-one (3.098 g, 19.3 mmol) in anhydrous dimethylformamide(DMF) (20 ml). A white precipitate appears immediately. The cooling bath is removed and the mixture is stirred at 25° C. (room temperature) for 5 mins. The mixture is diluted with benzene (200 ml), washed with H2O (5×80 ml) and brine, dired with MgSO4, filtered, and evaporated under reduced pressure to afford N-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)-azetidin-2-one (5.078 g) as an off white solid: ir(neat) 5.75, 8.08, 8.41, 11.92, and 12.18 cm-1 ; nmr(CDCl3) δ0.25 (s, 6), 0.98 (s, 9), 1.97 (m, 2), 2.05 (s, 3), 2.67 (dd, 1), 3.20 (dd, 1) 3.62 (m, 1), and 4.12 (t, 2); mass spectrum m/e 214 (M+ -57) and 172.
Workup
- customThe cooling bath is removed
- additionThe mixture is diluted with benzene (200 ml)
- washwashed with H2O (5×80 ml) and brine, dired with MgSO4
- filtrationfiltered
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b451d5a82cb1451ea760f01ab1cf409d
- Source dataset
- uspto-grants-1987_11
- Patent number
- US04707547
Reaction notes
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