(R)-3-(aminomethyl)hexanoic acid synthesis

8synthesis methods

Product Name:(R)-3-(aminomethyl)hexanoic acid
CAS Number:1314557-10-2
Molecular formula:C7H15NO2
Molecular Weight:145.2

Hexanoic acid, 3-[[[(1S)-1-phenylethyl]amino]methyl]-, (3S)-

1314557-03-3
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1314557-10-2
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Yield:80 % ee

Reaction Conditions:

with N-Bromosuccinimide in dimethyl sulfoxide at 20; for 2 h;Product distribution / selectivity;

Steps:

32

Example 32: Synthesis of 3-?-propyl-4-aminobutyric acid from [Villa] byoxidative debenzylation; 1.0 g of compound [Villa] is dissolved in dimethyl sulfoxide (20 mL) in a RB flask, followed by addition of N-bromosuccinimide (0.7 g). The reaction mixture is stirred at room temperature for 2 h or until all the generated bromine gets decolorized. DM water (20 mL) is added to the reaction mixture and stirred for another 20 min. Ethyl acetate (20 mL) is added to the reaction mixture followed by separation of the organic and aqueous phases. The aqueous phase is washed with 10 mL of ethyl acetate and the aqueous phases collected which contain the product (0.5g). Chiral HPLC analysis shows 80 % ee for f -3-rc-propyl-4- aminobutyric acid.

References:

WO2011/86565,2011,A1 Location in patent:Page/Page column 44