(4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate Chemical Properties

Boiling point:

339.8±17.0 °C(Predicted)

Density 

0.992±0.06 g/cm3(Predicted)

refractive index 

1.454-1.456

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Chloroform

pka

9.80±0.10(Predicted)

form 

Viscous Liquid

color 

Light yellow to green or light blue

λmax

204nm(EtOH)(lit.)

InChI

InChI=1S/C14H27NO4/c1-13(2,3)19-12(16)9-11-8-10(6-7-15)17-14(4,5)18-11/h10-11H,6-9,15H2,1-5H3/t10-,11-/m1/s1

InChIKey

HWSHVKNLMBMKSR-GHMZBOCLSA-N

SMILES

O1[C@H](CCN)C[C@H](CC(OC(C)(C)C)=O)OC1(C)C

CAS DataBase Reference

125995-13-3(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29153900

MSDS

• Language:English Provider:ACROS

(4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate Usage And Synthesis

Description

(4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate is an impurity of Atorvastatin. Atorvastatin is a drug used to lower cholesterol levels in the blood. It belongs to a class of drugs called HMG-CoA reductase inhibitors, and it works by blocking an enzyme that plays a role in the production of cholesterol.

Chemical Properties

Colorless to light yellow liqui

Uses

(4R,6R)-tert-Butyl-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxane-4-acetate is an useful synthetic intermediate.

Uses

An impurity of Atorvastatin (A791750).

Synthesis

General procedure for the synthesis of the target compound (CAS:125971-86-0) from (4R-cis)-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester: to a 5-gallon stainless steel reactor were added 250 g of Raney nickel (Ra-Ni), (4R,6R)-6-cyanomethyl-2,2-dimethyl-[1,3] tert-butyl dioxane-4-yl-acetate (1.0 kg, 3.71 mol), toluene (6 L), methanol (675 mL) and 6.5 M ammonia/methanol solution (800 mL). The reactor was sealed and pressure tested with nitrogen (N2) to 3.5 bar and purged three times with N2 at 3.5 bar. Subsequently, the reactor was purged with hydrogen (H2) three times to 3.5 bar, without turning on stirring during this process. After H2 pressurization to 3.5 bar, stirring was initiated and the reaction was carried out for 2-6 h. A slight exotherm was observed and the temperature increased to 30-40 °C. Stirring was continued until H2 absorption ceased, then stirring was continued at 30 to 40 °C for 30 min. The reaction mixture was cooled to 20-25 °C, the H2 source and stirrer were turned off, and the reactor was drained of H2. The stirrer was restarted, and the reactor was purged with N2 three times to 3.5 bar. The recovered nickel catalyst was filtered under nitrogen protection and the reactor and catalyst bed were washed with toluene (250 mL). The filtrates were combined and concentrated under reduced pressure to about 500 mL at no more than 55°C. [Note: the vacuum was broken with nitrogen after the concentration was completed]. Add saturated sodium chloride solution to the concentrate and stir under nitrogen protection for 10 minutes. Stop stirring and let stand to stratify. The lower aqueous phase was discarded and the organic phase was concentrated to give a yellow oily target product (1.054 kg, 104% yield, containing 7% residual toluene); 1H-NMR (400 MHz, CDCl3): δ 4.23-4.19 (m, 1H), 3.99-3.95 (m, 1H), 2.74 (t, J=7.1 Hz, 2H), 2.40-2.36 (m, 1H), 2.27-2.22 (m, 1H), 1.58-1.41 (m, 2H), 1.40 (s, 9H), 1.31 (s, 6H), 0.89 (s, 9H); low-resolution mass spectra (APCI) m/z 273 [M+H]+.

References

[1] Patent: US2005/239857, 2005, A1. Location in patent: Page/Page column 83
[2] Patent: US8563753, 2013, B2. Location in patent: Page/Page column 18; 19
[3] Patent: WO2007/49121, 2007, A1. Location in patent: Page/Page column 17-18
[4] Patent: CN104230880, 2016, B. Location in patent: Paragraph 0066-0067
[5] Tetrahedron Letters, 1992, vol. 33, # 17, p. 2283 - 2284

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