(3R,4R,5R)-5-(hydroxymethyl)piperidine-3,4-diol;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (3R,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethylpiperidine (0.527 g, 2.2. mmol) was dissolved in 0.5M HCl (5.3 ml) and ethanol (50 ml) and 5% palladium charcoal (300 mg) was added. The mixture was hydrogenated at 101 kPa and 20° C. for 18 hours. The reaction mixture was filtrated and concentrated to give the product in 93% (0.375 g) yield. 13C-NMR (50 MHz, D2O): d 70.7 og 68.1 (C-3 og C-4); 58.6 (C-5'); 46.2 og 44.4 (C-2 og C-6); 40.6 (C-5). 1H-NMR (500 MHz, D2O, Ph<1, ref. 4.63 ppm): d 3.72 (dd, 1H, H-5b',J5a',5b' =11.5, J5,5b' =3.3 Hz); 3.67 (ddd, 1H, H-3, J3,2ax =11.2, J3,4 =8.9,J3,2eq =4.9 Hz); 3.64 (dd, 1H, H-5a', J5 a',5b'=11.5,J5a',5 =6.2 Hz); 3.43 (ddd, 1H, H-2eq, J2eq,2ax =12.7, J2eq,3 =4.9, J2eq,6eq =2.0); 3.42 (dd, 1H, H-4, J4,5 =10.5, J4,3 =8.9 (Hz); 3.41 (ddd, 1H, H-6eq, J6eq,6ax =13.4, J6eq,5 =3.8, J6eq,2eq =2.0 Hz); 2.87, 12.7, J2ax,3 =11.2 Hz); 1.86 ppm (ddddd, 1H, H-5). If necessary, the piperidine could be chromatographed using ethanol/NH4OH (25% aqueous) (10:1) to give the free piperidine. Analytical calculation for C6H13NO3 : C: 48.97; H: 8.90; N: 9.52. Found: C: 48.46; H: 9.33; N: 9.17. The reaction mixture was filtrated concentrated to give the product in 93% (0.375 g) yield If necessary, the piperidine could be chromatographed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isofagomine free base (30 mg) was dissolved in MeOH (5 mL) and 4 N HCl (0.5 mL) in isopropanol and acetone (4.0 mL). The sample was stored refrigerated overnight and filtered. Crystals were observed in the solution. However, when filtered, the product was a yellow substance having a glue-like consistency. filtered However, when filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isofagomine free base (30 mg) was dissolved in MeOH (5 mL) and 4 N HCl (0.5 mL) in isopropanol and acetone (4.0 mL). The sample was stored refrigerated overnight and filtered. Crystals were observed in the solution. However, when filtered, the product was a yellow substance having a glue-like consistency. filtered However, when filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (3R,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethylpiperidine (0.527 g, 2.2. mmol) was dissolved in 0.5M HCl (5.3 ml) and ethanol (50 ml) and 5% palladium charcoal (300 mg) was added. The mixture was hydrogenated at 101 kPa and 20° C. for 18 hours. The reaction mixture was filtrated and concentrated to give the product in 93% (0.375 g) yield. 13C-NMR (50 MHz, D2O): d 70.7 og 68.1 (C-3 og C-4); 58.6 (C-5'); 46.2 og 44.4 (C-2 og C-6); 40.6 (C-5). 1H-NMR (500 MHz, D2O, Ph<1, ref. 4.63 ppm): d 3.72 (dd, 1H, H-5b',J5a',5b' =11.5, J5,5b' =3.3 Hz); 3.67 (ddd, 1H, H-3, J3,2ax =11.2, J3,4 =8.9,J3,2eq =4.9 Hz); 3.64 (dd, 1H, H-5a', J5 a',5b'=11.5,J5a',5 =6.2 Hz); 3.43 (ddd, 1H, H-2eq, J2eq,2ax =12.7, J2eq,3 =4.9, J2eq,6eq =2.0); 3.42 (dd, 1H, H-4, J4,5 =10.5, J4,3 =8.9 (Hz); 3.41 (ddd, 1H, H-6eq, J6eq,6ax =13.4, J6eq,5 =3.8, J6eq,2eq =2.0 Hz); 2.87, 12.7, J2ax,3 =11.2 Hz); 1.86 ppm (ddddd, 1H, H-5). If necessary, the piperidine could be chromatographed using ethanol/NH4OH (25% aqueous) (10:1) to give the free piperidine. Analytical calculation for C6H13NO3 : C: 48.97; H: 8.90; N: 9.52. Found: C: 48.46; H: 9.33; N: 9.17. The reaction mixture was filtrated concentrated to give the product in 93% (0.375 g) yield If necessary, the piperidine could be chromatographed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isofagomine free base (30 mg) was dissolved in MeOH (5 mL) and 4 N HCl (0.5 mL) in isopropanol and acetone (4.0 mL). The sample was stored refrigerated overnight and filtered. Crystals were observed in the solution. However, when filtered, the product was a yellow substance having a glue-like consistency. filtered However, when filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isofagomine free base (30 mg) was dissolved in MeOH (5 mL) and 4 N HCl (0.5 mL) in isopropanol and acetone (4.0 mL). The sample was stored refrigerated overnight and filtered. Crystals were observed in the solution. However, when filtered, the product was a yellow substance having a glue-like consistency. filtered However, when filtered

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (3R, 4R, 5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-piperidine, (12, 0.527 g, 2.2. mmol) was dissolved in 0.5M HCl (5.3 ml) and ethanol,(50 ml), 5% palladium charcoal (300 mg) was added. The mixture was hydrogenated at 101 kPa and 20° C. for 18 h. The reaction mixture was filtrated and concentrated to give the product in 93% (0.375 g) yield. 13C-NMR (50 MHz, D2O):δ70.7 and 68.1 (C-3 and C-4); 58.6 (C-5'); 46.2 and 44.4 (C-2 and C-6); 40.6 (C-5). 1H-NMR (500 MHz, D2O, PH<1, ref. HOD 4.63 ppm):δ3.72 (dd, 1H, H-5b', J5a',5b' =11.5, J5,5b' =3.3 Hz); 3.67 (ddd, 1H, H-3, J3,2ax =11.2, J3,4 =8.9, J3,2eq =4.9 Hz); 3.64 (dd, 1H, H-5a', J5a',5b' =11.5, J5,5b' =6.2 Hz); 3.43 (ddd, 1H, H-2eq, J2eq,2ax =12.7, J2eq,3 =4.9. J2eq,6eq =2.0); 3.42 (dd, 1H, H-4, J4,5 =10.5, J4,3 =8.9 (Hz); 3.41 (ddd, 1H, H-6eq, J6eq,6ax =13.4, J6eq,5 =3.8, J6eq,2eq =2.0 Hz); 2.87, 12.7, J2ax,3 =11.2 Hz); 1.86 ppm (ddddd, 1H, H-5). If necessary the piperidine could be chromatographed using ethanol/NH4OH (25% aq) 10:1 to give the free piperidine [α]D20 =+19.6° (c 0.85, EtOH). MS (CI, NH3): m/z 148 (M+H+). Anal. Calc. for C6H13NO3 : C,48.97; H, 8.90; N, 9.52. Found: C, 48.46; H, 9.33; N, 9.17. The reaction mixture was filtrated concentrated to give the product in 93% (0.375 g) yield If necessary the piperidine could be chromatographed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (3R,4R,5R)-3-Benzyloxy-4-hydroxy-5-hydroxymethylpiperidine (0.527 g, 2.2. mmol) was dissolved in 0.5M HCl (5.3 ml) and ethanol (50 ml) and 5% palladium charcoal (300 mg) was added. The mixture was hydrogenated at 101 kPa and 20° C. for 18 hours. The reaction mixture was filtrated and concentrated to give the product in 93% (0.375 g) yield. 13C-NMR (50 MHz, D2O): d 70.7 og 68.1 (C-3 og C-4); 58.6 (C-5'); 46.2 og 44.4 (C-2 og C-6); 40.6 (C-5). 1H-NMR (500 MHz, D2O, Ph<1, ref. 4.63 ppm): d 3.72 (dd, 1H, H-5b',J5a',5b' =11.5, J5,5b' =3.3 Hz); 3.67 (ddd, 1H, H-3, J3,2ax =11.2, J3,4 =8.9,J3,2eq =4.9 Hz); 3.64 (dd, 1H, H-5a', J5 a',5b'=11.5,J5a',5 =6.2 Hz); 3.43 (ddd, 1H, H-2eq, J2eq,2ax =12.7, J2eq,3 =4.9, J2eq,6eq =2.0); 3.42 (dd, 1H, H-4, J4,5 =10.5, J4,3 =8.9 (Hz); 3.41 (ddd, 1H, H-6eq, J6eq,6ax =13.4, J6eq,5 =3.8, J6eq,2eq =2.0 Hz); 2.87, 12.7, J2ax,3 =11.2 Hz); 1.86 ppm (ddddd, 1H, H-5). If necessary, the piperidine could be chromatographed using ethanol/NH4OH (25% aqueous) (10:1) to give the free piperidine. Analytical calculation for C6H13NO3 : C: 48.97; H: 8.90; N: 9.52. Found: C: 48.46; H: 9.33; N: 9.17. The reaction mixture was filtrated concentrated to give the product in 93% (0.375 g) yield If necessary, the piperidine could be chromatographed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isofagomine free base (30 mg) was dissolved in MeOH (5 mL) and 4 N HCl (0.5 mL) in isopropanol and acetone (4.0 mL). The sample was stored refrigerated overnight and filtered. Crystals were observed in the solution. However, when filtered, the product was a yellow substance having a glue-like consistency. filtered However, when filtered