ChemicalBook CAS DataBase List BOC-4-AMINOBENZYLALCOHOL

BOC-4-AMINOBENZYLALCOHOL synthesis

10synthesis methods

Product Name:BOC-4-AMINOBENZYLALCOHOL
CAS Number:144072-29-7
Molecular formula:C12H17NO3
Molecular Weight:223.27

24424-99-5 Synthesis

24424-99-5
832 suppliers
$13.50/25G

623-04-1 Synthesis

623-04-1
355 suppliers
$6.00/1g

144072-29-7
89 suppliers
$8.00/250mg

Yield: 100%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in tetrahydrofuranHeating / reflux;

Steps:

10
To a solution of p-amino-benzylalcohol (1 g, 8.12 mmol, 1 eq) in 80 mL of anhydrous THF were added DIEA (1.4 mL, 8.12 mmol, 1 eq) and BoC₂O (1.9 mL, 8.12 mmol, 1 eq). The mixture was heated to reflux overnight, then cooled down and evaporated under vacuum. The residue was dissolved in EtOAc. The organic layer was washed with a 0.1 N HCl solution, dried over MgSO₄, filtered and evaporated under vacuum. The crude product was purified by column chromatography on silica gel (Hex-EtOAc, 1:1, v/v) to give 1.85 g of product (quantitative yield): ¹H NMR δ 0.1.49 (9H, s), 2.17 (IH, s), 4.53 (2H₅ s), 6.83 (IH, s), 7.19 (2H, d, J = 8.5 Hz), 7.28 (2H, d, J = 8.2 Hz); ¹³ C NMR δ 28.28, 64.54, 80.37, 118.49, 127.59, 135.31, 137.46, 152.72.

References:

ENZON PHARMACEUTICALS, INC. WO2008/34124, 2008, A2 Location in patent:Page/Page column 72-73