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A suspension (3S)-I- [ (S)-L-PHENETHYL]-5-OXO-3-PYRROLIDINE-CARBOXYLIC acid (82.3 g, 352.3 mmol) in ET20 (200 mL) is added in small portions to A slurry of LiAlH4 (17.4 g, 459 mmol) in ET20 (700 mL). The mixture begins to reflux during the addition; the addition funnel containing the suspension is rinsed with Et20 (2 x 50 mL). The mixture is heated in a 50C oil bath for an additional 2 h, allowed to cool to rt, and further cooled using an ice bath. The mixture is carefully treated with H20 (62 mL). The resulting precipitate is filtered, rinsed with ET20, and discarded. The filtrate is concentrated to an oil. When EtOAc is added to the oil, a solid began to form. Hexane is added, and the mixture is filtered and the solid is dried to afford 43.3 g of the desired product. [?] 25D =-71 (c 0.94, CHC13) ;'H NMR (400 MHz, CDC13) 5 7.20-7. 45,3. 60-3.70, 3.40-3. 60,3. 19,3. 05-3.15, 2.35-2. 55,2. 25-2.35, 1.95-2. 10, 1.75-1. 90,1. 42; HRMS (FAB) calcd for CL3HLNO (MH+) 206.1545, found 206.1532. |
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With lithium aluminium tetrahydride; In diethyl ether; at 50℃; for 2h; |
A suspension (3S)-1-[(S)-1-phenethyl]-5-oxo-3-pyrrolidine-carboxylic acid (82.30 g, 352.8 mmol) in Et2O (200 mL) was added in small portions to a slurry of LiAlH4 (17.41 g, 458.6 mmol) in Et2O (700 mL). The mixture began to reflux during the addition. The addition funnel containing the suspension was rinsed with Et2O (2×50 mL), and the mixture was heated in a 50 C. oil bath for an additional 2 h and first allowed to cool to rt and then further cooled using an ice bath. The mixture was carefully treated with H2O (62 mL). The resulting precipitate was filtered, rinsed with Et2O, and discarded. The filtrate was concentrated to a yellow oil. When EtOAc was added to the oil, a solid began to form. Hexane was then added and removed by filtration and dried to afford 43.3 g as a white solid. [?]25D=-71 (c 0.94, CHCl3). MS (EI) m/z 205 (M+), 191, 190, 128, 105, 91, 86, 84, 79, 77, 51. |
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With lithium aluminium tetrahydride; In diethyl ether; at 50℃; for 2h;Heating / reflux; |
A suspension (36)-L- [ (-L-PHENETHYL]-5-OXO-3-PYRROLIDINE-CARBOXYLIC acid (82.30 g, 352.8 mmol) in Et2O (200 mL) is added in small portions to a slurry of LIALH4 (17.41 g, 458.6 mmol) in ET20 (700 mL). The mixture begins to reflux during the addition. The addition funnel containing the suspension is rinsed with Et20 (2 x 50 mL), and the mixture is heated in a 50 C oil bath for an additional 2 h and first allowed to cool to rt and then further cooled using an ice bath. The mixture is carefully treated with H2O (62 mL). The resulting precipitate is filtered, rinsed with ET20, and discarded. The filtrate is concentrated to a yellow oil. When EtOAc is added to the oil, a solid began to form. Hexane is then added, and the mixture is filtered and the solid is dried to afford 43.3 g. [alpha] U =-71 (c 0.94, CHCl3) ; 1H NMR (400 MHz, CDC13) 8 7.20-7. 45,3. 60-3.70, 3.40-3. 60,3. 19,3. 05-3.15, 2.35-2. 55,2. 25- 2.35, 1.95-2. 10,1. 75-1.90, 1.42 ; HRMS (FAB) calcd for C13H19NO (MH+) 206.1545, found 206.1532. |
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With lithium aluminium tetrahydride; In diethyl ether; at 50℃; for 2h;Heating / reflux; |
(3S)-1-[(S)-1-Phenethyl]-3-(hydroxymethyl)pyrrolidine: [CHEMMOL-00032] [0398] A suspension (3S)-1-[(S)-1-phenethyl]-5-oxo-3-pyrrolidine-carboxylic acid (82.30 g, 352.8 mmol) in Et2O (200 mL) was added in small portions to a slurry of LiAlH4 (17.41 g, 458.6 mmol) in Et2O (700 mL). The mixture began to reflux during the addition. The addition funnel containing the suspension was rinsed with Et2O (2×50 mL), and the mixture was heated in a 50 C. oil bath for an additional 2 h and first allowed to cool to rt and then further cooled using an ice bath. The mixture was carefully treated with H2O (62 mL). The resulting precipitate was filtered, rinsed with Et2O, and discarded. The filtrate was concentrated to a yellow oil. When EtOAc was added to the oil, a solid began to form. Hexane was then added and removed by filtration and dried to afford 43.3 g as a white solid. [alpha]25D=-71 (c 0.94, CHCl3). MS (EI) m/z 205 (M+), 191, 190, 128, 105, 91, 86, 84, 79, 77, 51. |