Hydrochloric Acid → HCID 67071612, compound

Participants

Reaction Steps

(S)-1-{2-[4-(6-isopropoxypyridin-3-yloxy)phenyl]ethyl}-2-methylpropylamine Borane-THF (2.87 ml, 2.87 mmol) is added dropwise under argon at 0° C. to 1-[4-(6-isopropoxypyridin-3-yloxy)phenyl]-4-methylpentan-3-one O-benzyloxime (310 mg, 0.717 mmol) in 15 ml of anhydrous THF. Then, (S)-1-[([1,3,2]dioxaborolan-2-yloxy)-diphenylmethyl]-2-methylpropylamine (23.3 mg) is added and the mixture is stirred for 2 days. Following addition of twice 1.5 ml of borane-THF stirring is continued for 4 h each time. % N hydrochloric acid is carefully added for hydrolysis, the mixture is rendered alkaline with aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic phase is separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 160 mg (68%), M+H+: 329.3. Chiral chromatography is performed (Chiralcel OD-H, heptane:ethanol=5:1+0.1% DEA) to obtain the enantiomers (R)-1-{2-[4-(6-isopropoxypyridin-3-yloxy)phenyl]ethyl}-2-methylpropylamine (RF: 4.442 min), Yield: 49 mg (21%), M+H+: 329.3. (S)-1-{2-[4-(6-Isopropoxypyridin-3-yloxy)phenyl]ethyl}-2-methylpropylamine (RF: 5.965 min), Yield: 50 mg (21%), M+H+: 329.3.

Provenance & Evidence