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R-3-aMnio-butanol

(R)-3-Amino-butan-1-ol

CAS: 61477-40-5

Molecular Formula: C4H11NO

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R-3-aMnio-butanol - Names and Identifiers

Name (R)-3-Amino-butan-1-ol
Synonyms DOLUTEGRAVIR2
R-3-aMnio-butanol
Dolutegravir INT 2
R-3-amino-1-butanol
(3R)-3-Amino-1-butanol
(3R)-3-aMinobutan-1-ol
(R)-3-Amino-butan-1-ol
1-Butanol,3-aMino-, (3R)-
(-)-(R)-3-aMinopropan-1-ol
CAS 61477-40-5
EINECS 640-387-9

R-3-aMnio-butanol - Physico-chemical Properties

Molecular FormulaC4H11NO
Molar Mass89.14
Density0.927
Boling Point168℃
Flash Point56℃
pKa15.00±0.10(Predicted)
Storage Conditionunder inert gas (nitrogen or Argon) at 2–8 °C
Refractive Index1.4530 to 1.4570
UseUses (R)-3-aminobutanol can be used as an intermediate in the preparation of compounds with HIV integrase inhibitory activity.

R-3-aMnio-butanol - Risk and Safety

UN IDs2735
Hazard Class8
Packing GroupⅢ

R-3-aMnio-butanol - Upstream Downstream Industry

Downstream Products(4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-4-Methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxaMide
(4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione

R-3-aMnio-butanol - Uses and synthesis methods

Introduction

(R)-3-aminobutanol is an alcohol organic substance, which is a key intermediate for many chiral drugs.

application

(R)-3-aminobutanol,(R)-3-amino-1-butanol, colorless or light yellow liquid, easily soluble in tetrahydrofuran, ethanol, water and other solvents, is a key intermediate for many chiral drugs. For example, J.Org.Chem.,1977,42:1650, reported that it is a key intermediate of the anti-tumor drug 4-methylcyclophosphamide; Tetrahed.Lett.,1988,29:231, reported that it is an important intermediate in the synthesis of penicilline antibiotics; Drugs.OftheFuture2012,37:697, reported that it is a key intermediate in the synthesis of the chiral six-membered ring of the anti-AIDS drug duluvir.

Preparation

Step 1:(R) Synthesis of methyl-3-aminobutyrate

240g of methanol and 50g(R)-3-aminobutyric acid are put into the clean reaction bottle, cooled with ice water, the temperature drops to 0~10 ℃, and 66.4g of thionyl chloride is slowly added dropwise. After the dripping is completed, the temperature is raised until the reflux reaction, until the raw material disappears. The reaction liquid is directly concentrated under reduced pressure to obtain the product. Yield: 98.5%, purity: 99.7%,ee:99.9%.

Step 2:(R)-Synthesis of methyl 3-benzyloxyamidobutyrate

50g(R)-3-aminobutyrate methyl ester hydrochloride, 400g of water and 41.4g of sodium carbonate are slowly put into the clean four-mouth bottle. After feeding, stirring and dissolving, the temperature dropped to 0~10 ℃, slowly adding 55.5g benzyl chloroformate dropwise, and controlling the temperature to 0~10 ℃. After dropping, raise the temperature to 20~30 ℃, keep the temperature and stir for 3~4h until the raw materials disappear. The reaction solution was added 200ML * 2 times of dichloromethane extraction, stratification, organic layers were combined, sodium sulfate was dried, and the product was concentrated under reduced pressure. Yield: 95.3%, purity 99.4%,ee:99.9%.

1HNMR(400MHZ,DMSO-D6):δ1.086~1.099(d,3H),δ2.367~2.411(m,1H),δ2.488~2.532(m,1H),δ3.576(s,3H),δ3.886~3.914(m,1H),δ5.012(s,2H),δ7.273~7.387(m,5H).

Step 3:(R)-Synthesis of 3-benzyloxyamidobutanol

50g(R)-3-benzyloxyamidobutyrate methyl ester and 250ML ethanol are put into the clean four-mouth bottle, and the mixture is stirred and dissolved. When the temperature drops to 0~10 ℃, 16.6g of potassium borohydride and 45.7g of magnesium chloride are added first, and the temperature is kept warm and stirred for 5h until the raw material detection reaction is completed, and hydrochloric acid aqueous solution is added dropwise for quenching. Filtration, the filtrate is concentrated under reduced pressure to no distillate, and white crystals are crystallized. Yield: 94.2%, purity: 99.2%,ee:99.9%.

Step 4:(R)-Synthesis of 3-aminobutanol

50g(R)-3-benzyloxyamidobutanol is added into the clean four-mouth bottle, 200ML of ethanol is added, g10wt%Pd/C is 2.5, the temperature is raised to 50~60 ℃, the hydrogen pressure is 0.4~0.6MPa, and the reaction is carried out until the raw materials disappear. Filtration, the filtrate is concentrated under reduced pressure to obtain oil, which is (R)-3-aminobutanol. Yield: 96.0%, purity 99.7%,ee:99.9%.

Last Update：2024-04-09 21:01:54
R-3-aMnio-butanol
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Nantong Reform Petro-Chemical CO., LTD.
Spot supply
Product Name: (R)-3-Amino-butan-1-ol Request for quotation
CAS: 61477-40-5
Tel: +86-17551318830
Email: r@reformchem.com­
Mobile: +86-17551318830
QQ: 3785839865 Click to send a QQ messageSend QQ message
Shanghai Yuanye Bio-Technology Co., Ltd.
Product Name: (3R)-3-Amino-1-butanol Visit Supplier Webpage Request for quotation
CAS: 61477-40-5
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
Wechat: 18301782025
Zouping Mingxing Chemical Co., Ltd.
Product Name: (R)-3-Aminobutan-1-ol Request for quotation
CAS: 61477-40-5
Tel: 0086-13605431940
Email: xuli678323@126.com
Mobile: +86-13605431940
QQ: 56860987 Click to send a QQ message
Wechat: 13605431940
WhatsApp: 13605431940
Shanghai Hanhong chemical Co.Ltd.
Product Name: R-3-amino-1-butanol Request for quotation
CAS: 61477-40-5
Tel: 021-54300995
Email: moresun@hanhonggroup.com
Mobile: 13916351815
QQ: 2355241827 Click to send a QQ messageSend QQ message
Shanghai Hanhong Scientific CO.,Ltd.
Product Name: (R)-3-Aminobutan-1-ol Request for quotation
CAS: 61477-40-5
Tel: 021-64541543
Email: paul@hanhonggroup.com
Mobile: 13918533501
QQ: 935888945 Click to send a QQ messageSend QQ message
View History
R-3-aMnio-butanol
Downstream Products for R-3-aMnio-butanol
(4R,12aS)-N-(2,4-difluorobenzyl)-7-benzylhydroxy-4-Methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxaMide
(4R,12aS)-7-(benzyloxy)-4-Methyl-3,4-dihydro-2H-[1,3]oxazino[3,2-d]pyrido[1,2-a]pyrazine-6,8(12H,12aH)-dione
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