727382-14-1

Basic information

• Product Name: (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile
• Synonyms: (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile
• CAS NO: 727382-14-1
• Molecular Formula: C₇H₁₄ClNOSi
• Molecular Weight: 191.73066
• Product Categories: Miscellaneous Reagents, Intermediates
• Mol File: 727382-14-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 233.8±20.0 °C(Predicted)
• Appearance: /
• Density: 1.002±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile(727382-14-1)
• EPA Substance Registry System: (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile(727382-14-1)

Safety Data

• Hazardous Substances Data: 727382-14-1(Hazardous Substances Data)

Usage

Description

(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile, also known as (3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile, is a useful research compound. ?Its molecular formula is C7H14ClNOSi and its molecular weight is 191.73 g/mol. The purity is usually 95%.

Uses

(3S)-4-Chloro-3-[(trimethylsilyl)oxy]butanenitrile is used in the synthesis of statins or HMG-CoA reductase inhibitors.

Synthesis

The synthesis of (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile is as follows:To a solution of (S)-4-chloro-3-hydroxy butanenitrile (52.5 g) in THF (150 mL) was added trimethyl silyl chloride (57.2 g) under inert atmosphere at 25 °C. The resulting reaction mixture was stirred for 10 min at 20°C. A solution of triethyl amine (53.4 g) in THF (100 mL) was added to above reaction mixture by maintaining reaction temperature below 40 °C. To the resulting reaction mixture catalytic amount of sodium iodide was added and stirred further for 5 h at 40°C. Reaction was monitored on GC as well TLC for complete conversion of starting material. After cooling to 0 °C, a 21% aqueous solution of sodium chloride (500 mL) was added and extracted with ethyl acetate (2 X 300 mL). Combined organic layer was dried with anhydrous sodium sulphate, filtered and concentrated under reduced pressure to obtain (3S)-4-Chloro-3-[(triMethylsilyl)oxy]butanenitrile as light brown liquid (84.0 g, 99%).

Upstream product

• 127913-44-4 (S)-4-chloro-3-hydroxy butyronitrile 
• 4039-32-1 lithium hexamethyldisilazane 
• 7677-24-9 trimethylsilyl cyanide 
• 106-89-8 epichlorohydrin 
• 75-77-4 chloro-trimethyl-silane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 154026-92-3 Tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate 

Relevant articles and documents

Chiral side chain of rosuvastatin calcium containing sulfone structure as well as preparation method and application of chiral side chain

The invention discloses a chiral side chain of rosuvastatin calcium containing a sulfone structure as well as preparation method and application of the chiral side chain. The chiral side chain D4-2 is prepared by taking D1-1 containing a thioether structure as a precursor; The D1-1 containing the thioether structure (Rz-S-) is synthesized through a brand-new process route and is further converted into a chiral side chain D4-2 containing the sulfone structure (Rz-SO2-), so that the separation and purification process of an intermediate is simplified; and after being modified by a sulfydryl-containing compound D1-M, the originally oily reaction intermediate is changed into a solid, so that the separation and purification effects of the intermediate are greatly improved. The chiral side chain D4-2 is used for preparing a high-grade intermediate R1 for synthesizing rosuvastatin calcium, the quality of R1 can be guaranteed, various indexes of the R1 product are excellent, and the cost is reduced; and the chiral side chain D4-2 is suitable for large-scale industrial production.

Stereoselective reduction of δ-hydroxy β-ketoesters to syndiol in achiral micellar system

A novel, efficient and stereo-selective process for synthesis of statin side chain, a key intermediate for statin type cholesterol lowering drugs such as Lipitor (atorvastatin) and Crestor (rosuvastatin) in achiral micellar media is reported. The key feature of this process is sodium borohydride reduction of δ-hydroxy β-ketoester in achiral micellar system in 92% de, thereby avoiding metal chelation methods which employ triakylborane, titanium (IV) isopropoxide or cerium (III) chloride prior to reduction.

A NOVEL, GREEN AND COST EFFECTIVE PROCESS FOR SYNTHESIS OF TERT-BUTYL (3R,5S)-6-OXO-3,5-DIHYDROXY-3,5-O-ISOPROPYLIDENE-HEXANOATE

The present invention provides a process of preparation of an intermediate useful for the preparation of statins more particularly the present invention relates to an eco-friendly and cost effective process for the preparation of tert -butyl (3R,5S)-6-oxo-3,5-dihydroxy- 3,5-O-isopropylidene-hexanoate [I].