Ammonium Chloride → HCID 57457828, compound

Participants

Reaction Conditions

Reaction Steps

Titanium isopropoxide (860 mg, 3.03 mmol) was added to a solution of ethyl 3-(dibenzylamino)propanoate (9.0 g, 30.3 mmol) in Et2O, cooled to 0° C., treated drop-wise with ethyl magnesium bromide (3M in Et2O, 30.3 mL) over 1 h, maintaining the temperature at 0˜4° C., then allowed to warm to RT and stirred overnight. The mixture was cooled to 0° C., treated with satd. NH4Cl, stirred at RT for 15 minutes, made basic with satd. NaHCO3 and extracted with EtoAc (2×). The combined organics were washed with brine, dried over MgSO4, concentrated and purified via silica gel chromatograph to give 1-(2-(dibenzylamino)ethyl)cyclopropanol (7.5 g, 88%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.20-7.15 (m, 8 H), 7.12-7.07 (m, 2 H), 3.45 (s, 4 H), 2.61-2.59 (m, 2 H), 1.57 (t, J=5.6 Hz, 2 H), 0.36-0.33 (m, 2 H), 0.30-0.17 (m, 2 H).

Provenance & Evidence