5-AMINO-1,3-DIHYDROXYMETHYLBENZENE

Compound 27:25 26 27[227] To a solution of 5-nitro-m-xylene-α, α'-diol 25 (1.07 g, 5.84 mmol) in methanol (50 mL) was added Pd/C (10percent, 311 mg, 0.29 mmol). Hydrogen was introduced to replace the air then the mixture was hydrogenated (HA solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq L1AIHA solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq L1AIH4 (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 percent). compound 7 (5.0 g, 32.6 mmol) was dissolved in THF (65.3 mL). TBSCl (12.30 g, 82 mmol) and imidazole (6.67 g, 98 mmol) were added and was stirred at rt overnight under Ar. The reaction mixture was diluted with EtOAc and was washed with sat'd NH4Cl and brine, dried aover Na2SO4 nd concentrated. The crude residue was purified by silica gel flash chromatography (EtOAc/hexanes, gradient, 0percent to 30percent) to obtain compound 37 as a yellow oil (13 g, 100percent yield). 1H NMR (400 MHz, CDCl3): delta 6.71 (s, 1H), 6.60 (s, 2H), 4.65 (s, 4H), 0.94 (s, 18H), 0.10 (s, 12H).A solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq L1AIH4 (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 %).A solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq L1AIH4 (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 %).A solution of dimethyl 5-aminoisophthalate (20.0 g, 96 mmol) in THF (350 mL) was added, dropwise, to a refluxing mixture of 3.75 eq LiAlFL (13.6 g, 358 mmol) in THF (440 mL) over one hour. The mixture was stirred at reflux for a further two hours, then cooled to room temperature and quenched by the careful addition of MeOH (27 mL) then water (40 mL). After stirring the quenched mixture for two hours it was filtered and concentrated to dryness. The residue was recrystallized (2X) from EtOAc to afford 15 as brownish-yellow crystals (10.2 g, 70 %).

Molecular Weight:153.18
XLogP3:-0.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:153.078978594
Monoisotopic Mass:153.078978594
Topological Polar Surface Area:66.5
Heavy Atom Count:11
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes