ChemicalBook CAS DataBase List (S)-(+)-2-INDOLINEMETHANOL

(S)-(+)-2-INDOLINEMETHANOL synthesis

9synthesis methods

Product Name:(S)-(+)-2-INDOLINEMETHANOL
CAS Number:27640-33-1
Molecular formula:C9H11NO
Molecular Weight:149.19

79815-20-6 Synthesis

79815-20-6
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$17.46/5G

27640-33-1
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$45.00/10mg

Yield:27640-33-1 96%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran;diethyl ether;Inert atmosphere;

Steps:

Chiral Auxiliaries and Phosphoramidites

To a solution of (2S)-dihydro-1 H-indole-2-carboxylic acid 1 (1 .63 g, 10.0 mmol) in ether (50 mL) was added a solution of LiAIH4 in THE (2M, 7.5 mL, 15.0 mmol) under argon, and the mixture was stirred overnight. After completion of the reaction, the mixture was quenched with Na2SO41 0H20. The solidwas filtered off and washed with ethyl acetate, and the filtrate was dried over anhydrous Na2SO4. Themixture was filtered, and the solvent evaporated to give a residue, which was subjected to flash silica gelcolumn purification on an 1500 (hexane/ethyl acetate, 10-70%) to give 1 .44 g (96%) of compound 2 as agray solid. 1H NMR (500 MHz, CDCI3 ppm): O7.10 (1H, d, J7.5 Hz), 7.04 (1H, t, J7.5 Hz), 6.75 (1H, t, J7.5 Hz), 6.69 (1 H, d, J 7.5 Hz), 4.10-4.06 (2H, m), 3.75 (1 H, dd, J 11.0, 4.0 Hz), 3.60 (1 H, dd, J 11 .0, 6.0Hz), 3.12(1 H, dd, J 16.0, 9.0 Hz), 2.87(1 H, dd, J 16.0, 8.0 Hz); ESI MS for C9HllNOcalculated 149.2, observed [M÷H] 150.1.

References:

WO2019/6455,2019,A1 Location in patent:Page/Page column 37