TY - JOUR AU - Woods, B P; Orlandi, M; Huang, C Y; Sigman, M S; Doyle, A G JO - J. Am. Chem. Soc. VL - 139 PY - 2017 DO - 10.1021/jacs.7b03448 L3 - PubMed-ID: 28406622 SP - 5688 N1 - ; The corresponding amino alcohol (1 mmol) and dimethyl oxalate (1 mmol) were added under a flow of argon into a flame-dried 25 mL Schlenk tube containing a PTFE-coated stirring bar. Toluene (10 mL) was added by using a syringe and the suspension was heated to 90 °C. After 3 h, the mixture was allowed to cool to room temperature and the volatiles were removed in vacuo. The resulting solid was washed with cold toluene (2 × 2 mL) to give the analytically pure product.Analytical data found for L3c1H NMR: δ = 8.05 (d, J = 9.8 Hz, 2 H), 3.74–3.40 (m, 6 H), 0.87 (s, 18 H).13C NMR (75 MHz, DMSO-d6): δ = 160.21, 59.90, 59.41, 33.93, 26.86.MS (ESI-TOF): m/z calcd 289.2127 [M+H]+, 311.1941 [M+Na]+; found: 289.2120 [M+H]+, 311.1944 [M+Na]+.L71H NMR (300 MHz, DMSO-d6): δ = 9.10 (s, 2 H), 7.30–6.94 (m, 8 H), 5.16–5.03 (m, 2 H), 4.58–4.41 (m, 2 H), 3.21–3.12 (m, 2 H), 2.78–2.69 (m, 2 H).13C NMR: (75 MHz, DMSO-d6): δ = 160.60, 141.16, 139.79, 127.66, 126.63, 124.66, 123.59, 76.91, 61.43, 40.20 (shoulder of DMSO signal).MS (ESI-TOF): m/z calcd 352.1423 [M]+; found: 352.1429 [M]+ ER -