(S)-2-AMino-2-(4-trifluoroMethylphenyl)ethanol synthesis

5synthesis methods

Product Name:(S)-2-AMino-2-(4-trifluoroMethylphenyl)ethanol
CAS Number:287394-20-1
Molecular formula:C9H10F3NO
Molecular Weight:205.18

2-Propanesulfinamide, N-[(1S)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[4-(trifluoromethyl)phenyl]ethyl]-2-methyl-, [S(R)]-

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(S)-2-AMino-2-(4-trifluoroMethylphenyl)ethanol

287394-20-1
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Yield:287394-20-1 93%

Reaction Conditions:

Stage #1: (Rs,1S)-N-(2-(tert-butyldimethylsilyloxy)-1-(4-(trifluoromethyl)phenyl)ethyl)-2-methylpropane-2-sulfinamidewith hydrogenchloride in methanol at 20; for 3 h;
Stage #2: with sodium hydrogencarbonate in water;

Steps:

4.6.1. (S)-2-Amino-2-(4-fluorophenyl)ethanol 1a

General procedure: At first, (Rs,2S)-N-((tert-butyldimethylsilyloxy)-1-(4-fluorophenyl)ethyl)-2-methylpropane-2-sulfinamide 8a (0.280 g, 0.749 mmol) was dissolved in MeOH (10 mL) and then HCl/MeOH (4 M, 2.0 mL) was added. The mixture was stirred at room temperature for 3 h. The solvent was removed under vacuum and the residue neutralized with saturated NaHCO₃ (20 mL). The mixture was extracted with CH₂Cl₂/MeOH (10:1, 3 × 50 mL) and the organic phases dried (Na₂SO₄) and concentrated to give 0.11 g (93%) of (S)-2-amino-2-(4-fluorophenyl)ethanol as a white solid.

References:

Pan, Xingang;Jia, Liangbin;Liu, Xuejian;Ma, Haikuo;Yang, Wenqian;Schwarz, Jacob B. [Tetrahedron Asymmetry,2011,vol. 22,# 3,p. 329 - 337] Location in patent:experimental part

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References

1,2-Ethanediol, 1-[4-(trifluoromethyl)phenyl]-, (1R)-

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402-43-7 Synthesis

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