ChemicalBook CAS DataBase List methyl indoline-5-carboxylate

methyl indoline-5-carboxylate synthesis

6synthesis methods

Product Name:methyl indoline-5-carboxylate
CAS Number:141452-01-9
Molecular formula:C10H11NO2
Molecular Weight:177.2

1011-65-0
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$6.00/250mg

141452-01-9
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$16.00/100mg

Yield: 99%

Reaction Conditions:

with sodium cyanoborohydride;acetic acid at 0 - 20; for 1.08333 h;

Steps:

19.A
To a solution of lH-Indole-5-carboxylic acid methyl ester (1 g, 5.71 mmol) in 10 mL of acetic acid at 0 ⁰C, was added sodium cyanoborohydride (1.08 g, 17.18 mmol) over 5 minutes. The mixture was stirred at room temperature for Ih. Water (3 mL) was added and all the solvents were removed under vacuum. The residue was dissolved in ethyl acetate (150 mL) and saturated NaHCCh (150 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 75 mL). The combined extracts were washed with brine (150 mL), dried, filtered and evaporated. The residue was purified by flash chromatography (0-50% ethyl acetate in hexane + 0.1% triethylamine) to afford 0.99 g (99%) of 19a.

References:

BOEHRINGER INGELHEIM INTERNATIONAL GMBH;NEUROCRINE BIOSCIENCES, INC.;TRAN, Joe, A.;CHEN, Chen WO2010/149685, 2010, A1 Location in patent:Page/Page column 51