methyl 3-hydroxyazetidine-3-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Synthesized according to Scheme B1 and general procedure I from 4-(5-benzylbenzo[d]thiazol-2-yl)-3-fluorobenzaldehyde (0.057 g, 0.16 mmol) and methyl 3-hydroxyazetidine-3-carboxylate (0.031 g, 0.16 mmol) to give methyl 1-((4-(5-benzylbenzo[d]thiazol-2-yl)-3-fluorophenyl)methyl)-3-hydroxyazetidine-3-carboxylate. 1H NMR (300 MHz, CDCl3) δ ppm 8.37 (t, J=7.7 Hz, 1H), 7.93 (s, 1H), 7.84 (d, J=8.2 Hz, 1H), 7.21-7.35 (m, 8H), 4.15 (s, 2H), 3.93-4.07 (m, 7H), 3.52-3.67 (m, 2H). MS (ESI) m/z: Calculated: 462.1 Observed: 463.1 (M++1). Synthesized

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

Procedure: Synthesized according to Scheme B1 and general procedure I from 4-(5-benzylbenzofuran-2-yl)-3-fluorobenzaldehyde (0.100 g, 0.30 mmol) and methyl 3-hydroxyazetidine-3-carboxylate (0.058 g, 0.30 mmol) to give methyl 1-((4-(5-benzylbenzofuran-2-yl)-3-fluorophenyl)methyl)-3-hydroxyazetidine-3-carboxylate. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.91 (t, J=7.9 Hz, 1H), 7.40-7.61 (m, 2H), 7.15-7.36 (m, 8H), 6.26 (s, 1H), 4.04-4.10 (m, 1H), 4.04 (s, 2H), 3.70 (s, 3H), 3.68-3.69 (m, 1H), 3.63 (d, J=7.9 Hz, 1H), 3.12-3.18 (m, 4H). MS (ESI) m/z: Calculated: 445.2 Observed: 446.1 (M++1). Synthesized

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

Procedure: A reactor was charged with methyl 1-benzhydryl-3-hydroxyazetidine-3-carboxylate (1.6 g, 5.4 mmol), 10% Pd/C (0.300 g, 2.8 mmol), and glacial acetic acid (0.300 mL, 5.2 mmol) in MeOH (30 mL). The mixture was allowed to stir for 3 h under 50 psig of H2. The crude was filtered through Celite and rinsed with MeOH. After evaporation, the solid was rinsed with Et2O to give methyl 3-hydroxyazetidine-3-carboxylate as the acetic acid salt. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.74 (d, J=9.1 Hz, 2H), 3.69 (s, 3H), 3.44 (d, J=8.9 Hz, 2H), 1.88 (s, 3H). The crude was filtered through Celite rinsed with MeOH After evaporation the solid was rinsed with Et2O