(S)-3-Dimethylamino-3-phenylpropanol

Colorless liquid

A solution of the above-prepared 3-amino-3-phenylpropanol (1.5 kg)Was dissolved in 1.6 kg (88percent, 30 mol) of formic acid, Add 2.8kg (37percent, 35mo 1) formaldehyde solution, heated to reflux, the reaction 8h.The reaction was quenched, concentrated under reduced pressure, 2L7K was added, adjusted to pH 12 with 10percent aqueous sodium hydroxide solution, and extracted with 3L / 4 times ethyl acetate. Combined with ethyl acetateThe layers were washed twice with 6 L saturated brine. Dried and concentrated under reduced pressure to give 1.65 kg of (s) -3-dimethylamino-3-phenylpropanol, purity (HPLC): 97.36percent yield 93.02percent. Ethyl acetate recovery cycle.To a solution of (XIII) (0.12 g, 0.807 mmol) in acetonitrile was added, 30percent aq formaldehyde solution (0.325 mL) followed by sodium cyanoborohydride (0.081 g, 1.29 mmol) and it was allowed to stir at room temperature. A few drops of glacial acetic acid were added to maintain the pH near neutrality. The solution was stirred at room temperature for 2 h. After completion of the reaction (TLC), the reaction mixture was concentrated in vacuo. To the residue was added 2 N aq KOH (10 mL). It was then extracted with ethyl acetate (3x10 mL). The ethyl acetate layer was then washed with 1 N HCl (3x5 mL). The combined HCl extracts were basified with solid KOH and then extracted with ethyl acetate (3x10 mL). Combined organic extracts were washed with brine (10 mL), dried over anhydrous NaExample-15: Preparation of (+)-3-N, N-dimethyl amino-3-phenyI propanol; Same procedure as described in Ex. 1 but using 50 g. of (+)-3-N, N-dimethyl amino-3- phenyl propanoic acid, 750 ml of tetrahydrofuran (THF), 24.5 g. of sodium borohydride and 64 g. of methane sulfonic acid to provide the title compound.Wt: 40-42gr. (percentYield: 90.7percent); Purity by HPLC: 98percent; SOR: +44.4° (0.6percent CHCI3).Example -17: Preparation of (+)-3-N, N-dimethyl amino-3-phenyl propanol; Same procedure as described in Ex. 1 but using 50 g. of (+)-3-N, N-dimethyl amino-3- phenyl propanoic acid hydrochloride, 750 ml of tetrahydrofuran (THF), 24.6 g. of sodium borohydride and 87.08 g. of methane sulfonic acid to provide the title compound.Wt: 30-32gr. (percentYield: 82.26percent); SOR : (+) 43.56°(0.6percent in CHC1In a reaction flask was added 500ml three intermediate II 44.25g (0.25mol) were added successively 111.2 g of 88percent formic acid, 111.2 g of water, followed by addition of paraformaldehyde (1.0 mol), refluxed for 6h, cooled to room temperature, add 50percent sodium hydroxide to adjust to pH 13, extracted with ethyl acetate 140ml × 3, the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a yellow oil 3-dimethylaminopropyl-3-phenylpropionate alcohol (III) 44.61g, yield 99.6percent.

Molecular Weight:179.26
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:179.131014166
Monoisotopic Mass:179.131014166
Topological Polar Surface Area:23.5
Heavy Atom Count:13
Complexity:130
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes