(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol

Bezeichnung:(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol

CAS-Nr127852-28-2

Englisch Name:(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol

CBNumberCB5113482

SummenformelC10H8F6O

Molgewicht258.16

MOL-Datei127852-28-2.mol

(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol physikalisch-chemischer Eigenschaften

Schmelzpunkt	53-58℃
Siedepunkt	175.8±35.0 °C(Predicted)
Dichte	1.376±0.06 g/cm3(Predicted)
storage temp.	-20°C Freezer
Löslichkeit	Acetonitrile (Slightly), Chloroform (Slightly)
pka	13.99±0.20(Predicted)
Aggregatzustand	Powder
Farbe	White
Optische Rotation	[α]/D +27±1°, c = 1 in acetonitrile
maximale Wellenlänge (λmax)	272nm(MeOH)(lit.)
InChI	InChI=1/C10H8F6O/c1-5(17)6-2-7(9(11,12)13)4-8(3-6)10(14,15)16/h2-5,17H,1H3/t5-/s3
InChIKey	MMSCIQKQJVBPIR-RXMQYKEDSA-N
SMILES	C(C1C=C([C@H](O)C)C=C(C(F)(F)F)C=1)(F)(F)F \|&1:4,r\|
CAS Datenbank	127852-28-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-52/53-22
S-Sätze:	26-36/37/39-61
WGK Germany	3
Hazard Note	Irritant
HS Code	29062990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral

Gefahreninformationscode (GHS)

(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
White fine crystalline powder
Verwenden
(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol is an intermediate in the synthesis of Aprepitant (A729800), a novel selective neurokinin-1 (NK-1) receptor antagonist. In vitro studies using human liver microsomes indicate that Aprepitant is metabolised primarily by CYP3A4 with minor metabolism by CYP1A2 and CYP2C19, and no metabolism by CYP2D6, CYP2C9, or CYP2E1. Antiemetic.
Allgemeine Beschreibung
(R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethanol is a key intermediate for the synthesis of aprepitant, a potent human neurokinin-1 (NK-1) receptor.
Synthese

30071-93-3

7480-35-5

368-63-8

The general procedure for the synthesis of 1-[3,5-bis(trifluoromethyl)phenyl]ethanol from 3,5-bis(trifluoromethyl)phenylacetophenone and cis-1-amino-2,3-dihydro-1H-inden-2-ol was as follows: in Example 5, [RuCl2(p-cymene)]2 (18.4 g), (1S,2R)- cis-1-amino-2-inden-2-ol (9.0 g) and 1- (3,5-bis(trifluoromethyl)phenyl)ethan-1-one (3 kg) were dissolved in 2-propanol (21 L), stirred for 30 min and thoroughly degassed under vacuum. A 5M sodium hydroxide solution (28mL) was then added and the mixture was aged for 4-6 hours to ensure complete conversion of the feedstock. Upon completion of the reaction, the mixture was poured into 1N HCl (21L) and extracted with heptane (2 x 10.5L). The organic layers were combined, washed with brine, and 1,4-diazabicyclo[2.2.2]octane (740 g) was added. The solution was concentrated to nearly 4 mL/g of alcohol (KF < 200 μg/mL; 2-propanol < 5 vol%). The mixture was inoculated at 40°C and allowed to cool slowly to room temperature to form crystalline species, which were then further cooled to 0°C. The crystalline product was collected by filtration, washed with cold heptane and dried to give the DABCO complex in 75-80% yield and ee value >99%.
Einzelnachweise
[1] Patent: US2002/22725, 2002, A1
[2] Patent: US2002/52493, 2002, A1
[3] Patent: US2002/52494, 2002, A1
[4] Patent: US6432952, 2002, B1
[5] Patent: US2003/215456, 2003, A1

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