Triethylamine → HCID 86652291, compound

About 7.23 g of ethyl 3-aminopropionate hydrochloride, 15.71 g of triethylamine, and 10 ml of toluene were mixed in a round-bottom reaction flask cooled with an ice bath. To this mixture was added, in a dropwise fashion, a solution of 23.00 g of trimethylsilyl trifluoromethanesulfonate in 50 ml of toluene. The resulting mixture was stirred at room temperature for 39 hours to give a biphasic mixture. The top layer was transferred to another flask, and the bottom layer was extracted with 40 ml of toluene. The combined toluene solution was evaporated under vacuum. The residue was extracted with 100 ml of hexane, and the hexane layer was evaporated under vacuum, yielding ethyl 3-[bis(trimethylsilyl)amino]propionate (3-BTMSAEP) as a colorless oil (11.03 g, 90% yield). The 1H NMR data (C6D6, 25° C., referenced to tetramethylsilane) of the product are listed as follows: δ 3.91 (quartet, 2 H, OCH2 protons), 3.21 (multiplet, 2 H, NCH2CH2 protons), 2.36 (multiplet, 2 H, NCH2CH2 protons), 0.91 (triplet, 3 H, CH3 protons), 0.07 (singlet, 18 H, Si—CH3 protons). From the 1H NMR data, the structure of the product was determined to be as follows:

1. temperaturecooled with an ice bath
2. additionTo this mixture was added, in a dropwise fashion
3. customto give a biphasic mixture
4. customThe top layer was transferred to another flask
5. extractionthe bottom layer was extracted with 40 ml of toluene
6. customThe combined toluene solution was evaporated under vacuum
7. extractionThe residue was extracted with 100 ml of hexane
8. customthe hexane layer was evaporated under vacuum

ORD record

ord-748b82efd02d424ebd7b23c1b1d7d324

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08895670B2