Published TCIMAIL newest issue No.200
Maximum quantity allowed is 999
Bitte wählen Sie die Menge aus.
TCI Practical Example: The Mitsunobu Type SN2 Reaction Using BEHT Triflate Salt, an Intermediate of the Mitsunobu Reaction
We are proud to present the Mitsunobu type SN2 reaction of benzyl (S)-(-)-lactate and indoline using BEHT triflate, a bench-stable intermediate salt. BEHT triflate can be used in the Mitsunobu reaction with lower acidic amines.
Used Chemicals
Procedure
DIEA (0.17 mL, 1.00 mmol) was added to a suspension of benzyl (S)-(-)-lactate (180 mg, 1.00 mmol), indoline (119 mg, 1.20 mmol) and BEHT triflate (704 mg, 1.20 mmol, 1.2 eq.) in DCE (1 mL) at room temperature. The mixture was stirred at room temperature for one day. The reaction mixture was quenched with sat. NaHCO3 aq. (5 mL) and the aqueous layer was extracted with dichloromethane (3 × 5 mL). The combined organic layer was washed with brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 0:100 – 5:95 on silica gel) to give benzyl (R)-2-(indolin-1-yl)propanoate as a pale red oil (154 mg, 54% yield).
Experimenter's Comments
The reaction mixture was monitored by UPLC.
Analytical Data
Benzyl (R)-2-(Indolin-1-yl)propanoate
1H NMR (400 MHz, CDCl3); δ 7.30–7.26 (m, 3H), 7.18 (dd, J = 3.2, 7.2 Hz, 2H), 7.05 (d, J = 7.3 Hz, 1H), 7.00 (t, J = 7.3 Hz, 1H), 6.64 (t, J = 7.3 Hz, 1H), 6.39 (d, J = 7.3 Hz, 1H), 5.11 (d, J = 12.8 Hz, 1H), 5.07 (d, J = 12.8 Hz, 1H), 4.32 (q, J = 7.0 Hz, 1H), 3.53 (t, J = 8.4 Hz, 2H), 2.95 (t, J = 8.4 Hz, 2H), 1.49 (d, J = 7.0 Hz, 3H).
Lead Reference
- Universal Reagent for Mild and Stereospecific Nucleophilic Substitution of Alcohols with Amines
