(3S,4S)-Pyrrolidine-3,4-diol

To a solution of (3S, 4S)-1-benzylpynolidne-3, 4-diol (522 mg) in ethanol (15 mL) were added 10percent palladium-carbon (100 mg) and acetic acid (10 mL), and the mixture was reacted under pressurized hydrogen (40psi) at room temperature for 7 hours in Parr hydrogenation apparatus. The reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. To the resulting residue was added 4N hydrochloric acid-dioxane solution, and then the mixture was concentrated under reduced pressure to give the titled compound (373 mg) as a yellow solid (yield 99percent). MS(APCI)m/z; 104[M+H]Intermediate ((3S, 4S) -5) (77.3g, 0.4mol) was dissolved in 80percent aqueous ethanol (2.4L) was added 10percent Pd / C (7.0g), at room temperature through hydrogen (0.07MPa) reaction 2d. The catalyst was removed by filtration and the filtrate concentrated under reduced pressure, the residue was treated with absolute ethanol (2 × 250mL) with traces of water addition to give a yellow oil of Intermediate ((3S, 4S) -6) 37.5g, yield 90.9percent.Intermediate ((3S, 4S)-5) (77.3 g, 0.4 mol) was dissolved in an aqueous solution of ethanol (80percent), to which10percent Pd/C (7.0 g) was added. Hydrogen (0.07 MPa) was supplied, and the reaction was kept for 2 days at room temperature.The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. Anhydrous ethanol(23250 mL) was used to remove the trace amount of water from the residue to obtain intermediate ((3S, 4S)-6) as ayellow oil (37.5 g, yield: 90.9percent).MASS (ESI+) m/z = 104 (M+H)+.1 H NMR (400 MHz, DSO-d6): 2.60 (m, 2H), 3.02 (m, 2H), 3.83 (m, 2H), 4.81 (br s, 3H).The intermediate ((3S, 4S)-5) (77.3 g, 0.4 mol) Soluble in 80percent aqueous ethanol solution (2.4L), Add 10percent Pd/C (7.0g), The reaction was carried out at room temperature with hydrogen (0.07 MPa) for 2 d.The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure.The residue was stripped of water with anhydrous ethanol (2×250 mL) to give a yellow oily intermediate ((3S, 4S)-6) 37.5 g, yield: 90.9percent.General procedure: 10 percent Pd/C (1.50 g) was added to solution of 3a (7.50 g, 38.86 mmol) in ethanol (40 mL) under argon atmosphere, hydrogenated under 100 psi at room temperature for 24 h. The reaction mixture was filtered through celite pad, filtrate was evaporated in vacuo to get crude. The crude product was washed with n-pentane-diethyl ether mixture (1:1) (20 mL), decanted the organic layer and dried in vacuo yielding 3.28 g (82.0 percent) of light brown solid of compound 4a.To a solution of (3S, 4S)-1-benzylpynolidne-3, 4-diol (522 mg) in ethanol (15 mL) were added 10percent palladium-carbon (100 mg) and acetic acid (10 mL), and the mixture was reacted under pressurized hydrogen (40psi) at room temperature for 7 hours in Parr hydrogenation apparatus. The reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. To the resulting residue was added 4N hydrochloric acid-dioxane solution, and then the mixture was concentrated under reduced pressure to give the titled compound (373 mg) as a yellow solid (yield 99percent). MS(APCI)m/z; 104[M+H]Intermediate ((3S, 4S) -5) (77.3g, 0.4mol) was dissolved in 80percent aqueous ethanol (2.4L) was added 10percent Pd / C (7.0g), at room temperature through hydrogen (0.07MPa) reaction 2d. The catalyst was removed by filtration and the filtrate concentrated under reduced pressure, the residue was treated with absolute ethanol (2 × 250mL) with traces of water addition to give a yellow oil of Intermediate ((3S, 4S) -6) 37.5g, yield 90.9percent.Intermediate ((3S, 4S)-5) (77.3 g, 0.4 mol) was dissolved in an aqueous solution of ethanol (80percent), to which10percent Pd/C (7.0 g) was added. Hydrogen (0.07 MPa) was supplied, and the reaction was kept for 2 days at room temperature.The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. Anhydrous ethanol(23250 mL) was used to remove the trace amount of water from the residue to obtain intermediate ((3S, 4S)-6) as ayellow oil (37.5 g, yield: 90.9percent).MASS (ESI+) m/z = 104 (M+H)+.1 H NMR (400 MHz, DSO-d6): 2.60 (m, 2H), 3.02 (m, 2H), 3.83 (m, 2H), 4.81 (br s, 3H).The intermediate ((3S, 4S)-5) (77.3 g, 0.4 mol) Soluble in 80percent aqueous ethanol solution (2.4L), Add 10percent Pd/C (7.0g), The reaction was carried out at room temperature with hydrogen (0.07 MPa) for 2 d.The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure.The residue was stripped of water with anhydrous ethanol (2×250 mL) to give a yellow oily intermediate ((3S, 4S)-6) 37.5 g, yield: 90.9percent.General procedure: 10 percent Pd/C (1.50 g) was added to solution of 3a (7.50 g, 38.86 mmol) in ethanol (40 mL) under argon atmosphere, hydrogenated under 100 psi at room temperature for 24 h. The reaction mixture was filtered through celite pad, filtrate was evaporated in vacuo to get crude. The crude product was washed with n-pentane-diethyl ether mixture (1:1) (20 mL), decanted the organic layer and dried in vacuo yielding 3.28 g (82.0 percent) of light brown solid of compound 4a.

Molecular Weight:103.12
XLogP3:-1.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Exact Mass:103.063328530
Monoisotopic Mass:103.063328530
Topological Polar Surface Area:52.5
Heavy Atom Count:7
Complexity:58.7
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes