Reaktion #988239

Reaktionsgleichung

compound 1

2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)-ethanol

DAST

→

solid

Ausbeute 33.0%

1,8-Diethyl-1-(2-fluoroethyl)-1,3,4,9-tetrahydropyrano[3,4-b]indole

Ausbeute 33.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturbefore being cooled to 0° C.
2. 2
   Sonstigequenched with MeOH (1 mL)
3. 3
   workup.STIRRINGThe mixture was stirred an additional thirty minutes at room temperature
4. 4
   workup.ADDITIONsaturated NaHCO3 (10 mL) was added dropwise
5. 5
   ExtraktionThe resulting aqueous layer was extracted three times with CH2Cl2
6. 6
   TrocknenThe combined organic phases were dried with Na2SO4
7. 7
   Einengenconcentrated
8. 8
   Sonstigepurified by column chromatography

Vorschrift

To a stirred solution of compound 1 (136 mg, 0.5 mmol) in CH2Cl2 (2 mL) at −40° C. under argon, DAST (396 μL, 3.0 mmol, 6.0 eq) was slowly added in a dropwise manner. The resulting mixture was allowed to warm to room temperature and stirred for one hour before being cooled to 0° C. and quenched with MeOH (1 mL). The mixture was stirred an additional thirty minutes at room temperature, and then saturated NaHCO3 (10 mL) was added dropwise. The resulting aqueous layer was extracted three times with CH2Cl2. The combined organic phases were dried with Na2SO4, concentrated, and purified by column chromatography using 5:95:EtOAc:Hexane to give a yellow-white solid (45 mg, 33%): mp 118-119° C. 1HNMR (CDCl3, δ TMS): 0.88 (t, 3H), 1.37 (t, 3H), 1.94 (m, 2H), 2.29 (m, 2H), 2.78 (m, 2H), 2.86 (q, 2H), 3.99 (m, 2H), 4.57 (qq, 2H), 7.03-7.38 (m, 3H, Ar—H), 7.65 (br, 1H, NH). MS−: m/z 310 (MCl−), 274 ([M−H]−). Anal. (C17H22NOF): C, H, N.

Quelle