Compound 25
3-Amino-3-phenylpropan-1-ol
From: SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes
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InChIKey SEQXIQNPMQTBGN-UHFFFAOYSA-N
- 3-Amino-3-phenyl-propan-1-ol,
- (S)-3-Amino-3-phenylpropan-1-ol,
- DL-beta-Phenylalaninol,
- (1-Amino-3-hydroxyprop-1-yl)benzene,
- 3-phenyl-DL-beta-alaninol,
- (R)-3-Amino-3-phenylpropan-1-ol,
- 3-Amino-3-phenyl-1-propanol
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Compound 25 was prepared according to a modified literature procedure (Torre, O., Gotor-Fernández, V. & Gotor, V. Lipase-catalyzed resolution of chiral 1,3-amino alcohols: application in the asymmetric synthesis of (S)-dapoxetine. Tetrahedron: Asymmetry 17, 860–866 (2006)): Commercially available 3-amino-3-phenylpropanoic acid (842 mg, 5.00 mmol, 1.00 equiv) was slowly added to a solution of LiAlH4 (570 mg, 15.0 mmol, 3.00 equiv) in THF (25 ml) at 0 °C. The resulting mixture was allowed to warm to rt and heated at reflux for 3 h. The reaction mixture was allowed to cool to rt and was slowly quenched with H2O (5 mL) followed by sat aq NaHCO3 (5 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3 x 5 mL). The combined organic layers were washed with H2O (2 x 10 mL), brine (10 mL), dried over Na2SO4, filtered and concentrated to afford the pure amino alcohol 25 (693 mg, 92% yield) as colorless oil. 1H NMR (400 MHz, CDCl3): δ7.38-7.24 (m, 5H), 4.13 (dd, J = 8.2, 4.9 Hz, 1H), 3.88-3.76 (m, 2H), 2.45 (br s, NH2), 1.96-1.85 (m, 2H); 13C NMR (100 MHz, CDCl3): δ 146.4, 128.9, 127.3, 125.8, 62.6, 56.9, 39.6.
