[3-(benzyloxy)-1,2-oxazol-5-yl]Methanol

To a solution of methyl 3-benzyloxyisoxazole-5-carboxylate (2.33 g, 9.99 mmol, 1.00 eq) in methanol (50 mL) was added sodium borohydride (756 mg, 19.98 mmol, 2.00 eq) in portions. The resulting mixture was stirred at 15 °C for 3 hr. TLC (petroleum ether : ethyl acetate = 5 : 1) showed the reaction was completed. The mixture was poured into hydrochloric acid (0.2 M, 200 niL), and extracted with ethyl acetate (150 niL x 2). The combined organic layers were washed with saturated brine (200 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford (3-benzyloxyisoxazol-5-yl)methanol (1.85 g, 9.02 mmol, 90percent yield) as colorless oil. LC-MS (ESI) m/z: 206.1 [M+HExample 7A (0.52g, 2.23 mmol) was dissolved in methanol (25 mL) and treated with solid sodium borohydride (0.1 lOg, 2.90 mmol). The solution began foaming which subsidedapproximately 10 minutes later. The reaction mixture was stirred at room temperature for 20 hours. Methanol (50 mL) and 1 N aqueous HC1 (100 mL) were then added to the mixture which was subsequently stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo. The aqueous layer was extracted with dichloromethane (3x 100 mL). The combined organic washes were dried over anhydrous NaTo a solution of methyl 3-benzyloxyisoxazole-5-carboxylate (2.33 g, 9.99 mmol, 1.00 eq) in methanol (50 mL) was added sodium borohydride (756 mg, 19.98 mmol, 2.00 eq) in portions. The resulting mixture was stirred at 15 °C for 3 hr. TLC (petroleum ether : ethyl acetate = 5 : 1) showed the reaction was completed. The mixture was poured into hydrochloric acid (0.2 M, 200 niL), and extracted with ethyl acetate (150 niL x 2). The combined organic layers were washed with saturated brine (200 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford (3-benzyloxyisoxazol-5-yl)methanol (1.85 g, 9.02 mmol, 90percent yield) as colorless oil. LC-MS (ESI) m/z: 206.1 [M+HExample 7A (0.52g, 2.23 mmol) was dissolved in methanol (25 mL) and treated with solid sodium borohydride (0.1 lOg, 2.90 mmol). The solution began foaming which subsidedapproximately 10 minutes later. The reaction mixture was stirred at room temperature for 20 hours. Methanol (50 mL) and 1 N aqueous HC1 (100 mL) were then added to the mixture which was subsequently stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo. The aqueous layer was extracted with dichloromethane (3x 100 mL). The combined organic washes were dried over anhydrous NaTo a solution of methyl 3-benzyloxyisoxazole-5-carboxylate (2.33 g, 9.99 mmol, 1.00 eq) in methanol (50 mL) was added sodium borohydride (756 mg, 19.98 mmol, 2.00 eq) in portions. The resulting mixture was stirred at 15 C for 3 hr. TLC (petroleum ether : ethyl acetate = 5 : 1) showed the reaction was completed. The mixture was poured into hydrochloric acid (0.2 M, 200 niL), and extracted with ethyl acetate (150 niL x 2). The combined organic layers were washed with saturated brine (200 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford To a solution of methyl 3-benzyloxyisoxazole-5-carboxylate (2.33 g, 9.99 mmol, 1.00 eq) in methanol (50 mL) was added sodium borohydride (756 mg, 19.98 mmol, 2.00 eq) in portions. The resulting mixture was stirred at 15 C for 3 hours. The mixture was poured into hydrochloric acid (0.2 M, 200 mL), and then extracted with ethyl acetate (150 mL x 2). The combined organic layers were washed with saturated brine (200 mL x 2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford (3-benzyloxyisoxazol-5- yl)methanol (1.85 g, 9.02 mmol, 90% yield) as colorless oil. LC/MS (ESI) m/z· 206.0 [M+l] +.Example 7A (0.52g, 2.23 mmol) was dissolved in methanol (25 mL) and treated with solid sodium borohydride (0.1 lOg, 2.90 mmol). The solution began foaming which subsidedapproximately 10 minutes later. The reaction mixture was stirred at room temperature for 20 hours. Methanol (50 mL) and 1 N aqueous HC1 (100 mL) were then added to the mixture which was subsequently stirred for 2 hours at room temperature. The reaction mixture was concentrated in vacuo. The aqueous layer was extracted with dichloromethane (3x 100 mL). The combined organic washes were dried over anhydrous Na2S04(s), filtered and concentrated in vacuo leaving the title compound as a clear oil (0.4 g, 87%).To a solution of cyanic bromide (334 mg, 3.15 mmol, 1.05 eq) and triphenylphosphine (787 mg, 3.00 mmol, 1.00 eq) in dichloromethane (10 mL) was added a solution of (3-benzyl oxyisoxazol-5-yl)methanol (616 mg, 3.00 mmol, 1.00 eq) in dichloromethane (lOmL). The mixture was stirred at 15 C for 1 hour, then 2, 3, 4, 6, 7, 8, 9, 10- octahydropyrimido [l, 2-a]azepine (480 mg, 3.15 mmol, 1.05 eq) was added at 0 C. The resulting mixture was stirred at 0-15 C for another 14 hours. The solvent was concentrated in vacuum. The residue was further purified by silica gel column chromatography (Petroleum ether: Ethyl acetate = 5:1 to 4:1) to afford 2-(3-benzyloxyisoxazol-5-yl)acetonitrile (320 mg, 1.49 mmol, 50% yield) as a colorless oil. LC/MS (ESI) m/z 215.0 [M+l] +; -NMR (400MHz, CDCL) d 7.48 - 7.41 (m, 5H), 6.06 (s, 1H), 5.30 (s, 2H), 3.82 (s, 2H).

Molecular Weight:205.21
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:205.07389321
Monoisotopic Mass:205.07389321
Topological Polar Surface Area:55.5
Heavy Atom Count:15
Complexity:183
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes