benzyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate synthesis
- Product Name:benzyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)piperidine-1-carboxylate
- CAS Number:1380313-68-7
- Molecular formula:C19H28BNO4
- Molecular Weight:345.24
76-09-5
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Yield:1380313-68-7 78%
Reaction Conditions:
Stage #1: benzo[1,3,2]dioxaborolewith bis(cyclopentadienyl)titanium dichloride;potassium carbonate in tert-butyl methyl ether; for 0.5 h;
Stage #2: benzyl 4-bromo-1-piperidinecarboxylate in tert-butyl methyl ether at 80; under 760.051 Torr; for 24 h;Inert atmosphere;
Stage #3: 2,3-dimethyl-2,3-butane diolwith triethylamine in tert-butyl methyl ether at 20; for 1 h;Inert atmosphere;
Steps:
79 Example 79
Bis(cyclopentadiene)titanium dichloride (denoted as Cp2TiCl2, 0.01mmol, 2.5mg), potassium carbonate (denoted as K2CO3, 0.2mmol, 26.7mg), methyl tert-butyl ether (1mL) Add catecholborane (denoted as HBcat, 0.6mmol, 63μL) into a 38mL pressure tube in sequence, stir for 30min and add 1-Cbz-4-bromopiperidine (denoted as 1an, 0.2mmol, 44μL) in nitrogen Stir at 80°C for 24h under a (1atm) atmosphere, add triethylamine (0.6mmol, 84μL) and pinacol (0.6mmol, 70.8mg) after the reaction, and stir at room temperature for 1h. Then use petroleum ether/ethyl acetate (20:1, v/v) as the eluent to carry out column chromatography purification to obtain the structure compound represented by formula 2an (colorless and transparent liquid, 4-(2-4,4,5,5) -Tetramethyl-1,3,2-dioxaborolane) piperidine-1 carboxylic acid benzyl ester). The isolated yield is 78%.
References:
CN112645971,2021,A Location in patent:Paragraph 0226-0228
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