(R)-3-AMINO-1-BUTANOL Basic Information
| Product Name | (R)-3-AMINO-1-BUTANOL |
| Synonyms | R-3-amino-1-butanol;(3R)-3-Amino-1-butanol;1-Butanol,3-aMino-, (3R)-;(-)-(R)-3-aMinopropan-1-ol;(3R)-3-aMinobutan-1-ol;R-3-aMnio-butanol;Dolutegravir INT 2;DOLUTEGRAVIR2 |
| CAS | 61477-40-5 |
| MF | C4H11NO |
| MW | 89.14 |
| EINECS | 640-387-9 |
(R)-3-AMINO-1-BUTANOL Chemical Properties
| Boiling point | 168℃ |
| density | 0.927 |
| refractive index | 1.4530 to 1.4570 |
| Fp | 56℃ |
| storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C |
| solubility | soluble in Dichloromethane, DMSO |
| form | clear liquid |
| pka | 15.00±0.10(Predicted) |
| color | Colorless to Light orange to Yellow |
(R)-3-AMINO-1-BUTANOL Usage And Synthesis
|
Uses |
It is the key intermediate of many chiral drugs |
|
Description |
It is reported that it is the key intermediate of antitumor drug 4-methylcyclophosphamide, an important intermediate for the synthesis of penicillin antibiotics, and the key intermediate for the synthesis of hand-held six membered ring of anti AIDS drug truthvir |
|
Chemical Properties |
Soluble in tetrahydrofuran, ethanol, water and other solvents |
One of the preparation methods
Step 1: put 240g methanol and 50g (R) - 3-aminobutyric acid into the reaction bottle, cool it with ice water, drop the temperature to 0-10 ℃, and slowly add 66.4g sulfoxide chloride. After dropping, the temperature was raised to reflux reaction until the raw material disappeared. The reaction solution was directly concentrated under reduced pressure to obtain the product.
Step 2: put 50g (R) - 3-aminobutyric acid methyl ester hydrochloride and 400g water into a four mouth bottle, and slowly add 41.4g sodium carbonate. 5 g Benzyl Chloroformate was added slowly, and the temperature was controlled to 0-10 ℃. After dropping, the temperature was raised to 20-30 ℃ and stirred for 3-4 h until the raw material disappeared. The reaction solution was extracted with 200 ml * 2 dichloromethane, stratified, combined with organic layer, dried with sodium sulfate, and concentrated under reduced pressure.
Step 3: put 50g (R) - 3-benzyloxyamidobutyrate methyl ester and 250ml ethanol into a four mouth bottle, stir and dissolve. When the temperature drops to 0-10 ℃, 16.6g of potassium borohydride is put in first, and then 45.7g of magnesium chloride is put into the mixture, and then the mixture is stirred for 5h. After the detection and reaction of raw materials are finished, the hydrochloric acid solution is added to quench it. After filtration, the filtrate was concentrated to no distillate under reduced pressure to obtain white crystal.
Step 4: put 50g (R) - 3-benzyloxyamidobutanol into a four mouth bottle, add 200ml ethanol, 2.5G 10wt% Pd / C, raise the temperature to 50-60 ℃, and the hydrogen pressure is 0.4-0.6mpa until the raw material disappears. After filtration, the filtrate was concentrated under reduced pressure to obtain an oily substance (R) - 3-aminobutanol.
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