ChemicalBook CAS DataBase List (R)-2-Amino-2-(4-fluorophenyl)ethanol

(R)-2-Amino-2-(4-fluorophenyl)ethanol synthesis

6synthesis methods

Product Name:(R)-2-Amino-2-(4-fluorophenyl)ethanol
CAS Number:174770-74-2
Molecular formula:C8H10FNO
Molecular Weight:155.17

To a stirred solution of lithium aluminium hydride (1.0 M in THF, 11.9 ml, 11.9 mmol) at 0℃ was added 4- (R)-fluorophenylglycine (1.0 g, 5.9 mmol) portion wise over 1 hour. The mixture was stirred at room temperature for 16 hours. Water (0.45 ml), 4 NNaOH (0.45 ml) and water (1.34 ml) was added to the mixture and the mixture was stirred for 10 minutes before being filtered. The filtrate was concentrated to give a yellow residue, (R)-2-Amino-2-(4-fluorophenyl)ethanol.

93939-74-3 Synthesis

93939-74-3
203 suppliers
$26.00/250mg

174770-74-2
54 suppliers
$68.00/100mg

Yield:174770-74-2 88%

Reaction Conditions:

Stage #1: (R)-2-(4-fluorophenyl)glycinewith lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 17 h;
Stage #2: with sodium hydroxide in tetrahydrofuran;water; for 0.166667 h;

Steps:

104

To a stirred solution of lithium aluminium hydride (1.0 M in THF, 11.9 ml, 11.9 mmol) at0 C was added 4- (R)-fluorophenylglycine (1.0 g, 5.9 mmol) portion wise over 1 hour. The mixture was stirred at room temperature for 16 hours. Water (0.45 ml), 4 NNaOH (0.45 ml) and water (1.34 ml) was added to the mixture and the mixture was stirred for 10 minutes before being filtered. The filtrate was concentrated to give a yellow residue. Flash chromatography(CombiFlash,CH2Cl2/MeOH/NH3 = 90/10/1) gave productas a white solid (800 mg,88%). 1H NMR 8 3.25 (m, 1 H), 3.30 (m, 1 H), 3.40 (m, 1 H), 3.83 (m, 1 H), 4.77 (br s, 1 H), 7.06 (m, 2 H), 7.37(m, 2 H).

References:

WO2005/49033,2005,A1 Location in patent:Page/Page column 114