Trifluoroacetic acid → HCID 73553977, compound

A solution of 10.0 g (61.6 mmol) of benzyl acrylate and 19 mL (74.2 mmol) of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine in 75 mL of CH2Cl2 at 0° C. was treated with 0.5 mL (6.5 mmol) of TFA while maintaining the internal temperature at less than 3° C. The reaction was warmed to rt and stirred for 2.5 h. The reaction mixture was washed with 250 mL of 1N NaHCO3 and 250 mL of sat'd NaCl. The organic layer was dried over Na2SO4 and concentrated. The residue was purified on a 40L Biotage column using 19:1 v/v hexane/acetone as the eluant to afford 18 g (99%) of the title compound as a light yellow oil: RF: 0.28 (9:1 v/v hexane/acetone); 1H-NMR (500 MHz) δ 2.15-2.20 (m, 2H), 2.60 (m, 1H), 2.73-2.77 (m, 2H), 3.02 (m, 1H), 3.13 (m, 1H), 3.66-3.73 (m, 2H), 5.17 (s, 2H), 7.28-7.42 (m, 5H).

1. temperaturewhile maintaining the internal temperature at less than 3° C
2. washThe reaction mixture was washed with 250 mL of 1N NaHCO3 and 250 mL of sat'd NaCl
3. dry with materialThe organic layer was dried over Na2SO4
4. concentrationconcentrated
5. customThe residue was purified on a 40L Biotage column

ORD record

ord-17c097f1d26c470d9872f9d25b84cf04

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07479504B2