ChemicalBook CAS DataBase List (S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine

(S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine synthesis

9synthesis methods

Product Name:(S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine
CAS Number:132335-44-5
Molecular formula:C9H15NOS
Molecular Weight:185.29

5424-47-5 Synthesis

2-THIENYL-2-DIMETHYLAMINOETHYL KETONE HCL

5424-47-5
209 suppliers
$9.00/5g

(S)-(-)-N,N-Dimethyl-3-hydroxy-3-(2-thienyl)propanamine

132335-44-5
333 suppliers
$6.00/1g

Yield:132335-44-5 92.1%

Reaction Conditions:

with glucose dehydrogenase;D-glucose;Rhodosporidium toruloides carbonyl reductase 9 from Escherichia coli;NADPH;sodium hydroxide in aq. phosphate buffer; pH=7 at 30; for 4 h;Kinetics;Enzymatic reaction;enantioselective reaction;Temperature;

Steps:

In a 2-L bioreactor, 2a (1000mM), glucose (6000mM), NADP⁺ (0.75mM), and sonicated cells of co-expressing E. coli/RtSCR9-GDH (10gDCWL^-1) were mixed in a total volume of 1L phosphate buffer (100mM, pH 7.0). The resulting mixture was stirred at 30°C with 200rpm shaking for 240min. The pH was maintained at 7.0 with 2M NaOH during the reaction. After reaching completion, the pH was adjusted to 11-12 followed by extraction using ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and concentrated to give (S)- 3a. Yield: 92.1%. ¹H NMR (500MHz, DMSO-d₆): δ=7.36 (dd, J=4.9, 1.2Hz, 1H), 6.93 (m, 2H), 5.79 (s, 1H), 4.86 (m, 1H), 2.30 (qt, J=12.0, 7.1Hz, 2H), 2.12 (s, 6H), 1.79 (m, 2H). ¹³C NMR (126MHz, DMSO-d₆): δ=150.72, 126.40, 123.79, 122.51, 67.39, 55.96, 45.15, 36.92. [α]²⁵_D=-4.9° (c=10mg/mL, ethyl acetate).

References:

Chen, Xiang;Liu, Zhi-Qiang;Lin, Chao-Ping;Zheng, Yu-Guo [Bioorganic Chemistry,2016,vol. 65,p. 82 - 89]