Borane;tetrahydrofuran → 2,3-Dihydro-1H-pyrido[2,3-b][1,4]oxazine

HRID 417925Notes

Reaction equation

HRID 417925 reaction equation
[NH:1]1[C:6](=O)[CH2:5][O:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.B.C1COCC1>C1COCC1>[NH:1]1[CH2:6][CH2:5][O:4][C:3]2[N:8]=[CH:9][CH:10]=[CH:11][C:2]1=2

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 159259881H,2H,3H-pyrido(2,3-b)(1,4)oxazin-2-one

Product 1

HCID 151279022,3-Dihydro-1H-pyrido[2,3-b][1,4]oxazineYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using 1H-pyrido[2,3-b][1,4]oxazin-2-one (0.3 g, 2 mmol) and borane-THF (8 mL of a 1M solution in THF, 8 mmol) in THF (20 mL) to yield the title compound as a yellow solid (180 mg, 66%). δH (CDCl3) 3.38-3.46 (2H, m), 3.85 (1H, br s), 4.38-4.45 (2H, m), 6.74 (1H, dd, J 7.7, 4.9 Hz), 6.83-6.88 (1H, m), 7.61 (1H, dd, J 4.7, 1.5 Hz).

Sources & evidence

ORD record
ord-c4fb582c62a64a478e3392351cc32d86
Source dataset
uspto-grants-2012_01
Patent number
US08093238B2

Reaction notes

Loading…