Triethylamine → N-(t-butyldimethylsilyl)-4-(2-acetoxyethyl)azetidin-2-one

HRID 1493463Notes

Reaction equation

C(N(CC)CC)C.[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[C:16]([O:19][CH2:20][CH2:21][CH:22]1[NH:25][C:24](=[O:26])[CH2:23]1)(=[O:18])[CH3:17]>CN(C)C=O>[Si:8]([N:25]1[CH:22]([CH2:21][CH2:20][O:19][C:16](=[O:18])[CH3:17])[CH2:23][C:24]1=[O:26])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 25 °C

Procedure

Triethylamine (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-b98b40dcbaf94d50afd01423a7e5eb97
Source dataset: uspto-grants-1991_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05021566

Reaction notes

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