Structure of 64658-22-6
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 64658-22-6 |
Formula : | C9H12O2 |
M.W : | 152.19 |
SMILES Code : | C[C@H](CO)OC1=CC=CC=C1 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Ru(H)2{(R)-Tol-BINAP{R,R}-dpen}; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 22℃; under 3040.2 Torr; for 0.333333h;Glovebox; | General procedure: 0.01 mmol (8.1 mg) of RuCl2{(R,R)(Ph2PCH(Ph)CH(Me)NH2}2 (12a), and 0.15 mmol (16.8 mg) of KOtBu were weighed out into two separate NMR tubes in a glove box. 1 mL of freshly distilled THF was then added to each of the NMR tubes and then shaken to dissolve the compounds. A low-pressure glass reactor was then charged with 0.5 mmol of amide and then purged for 10 min with H2. The catalyst precursor solution was then cannulated into the reactor under H2 followed by KOtBu solution and a 2 mL THF wash. The reactor was then pressurized to 4 atm H2. The reaction was then monitored every 20 min by removing a sample and recording the 1H NMR. Several amides and catalysts have been screened using this reaction, and determined the enantiomeric excess of the product alcohols. The data obtained is summarized in table 7, below. Percentage conversion was determined by 1H NMR. Percentage enantiomeric excess (ee) was determined by HPLC using CHIRALPAK TM IB Column, reaction conditions: 4 atm H2, room temperature (22 C.), [Substrate]=0.125 M (4 mL THF). |