Diethyl Ether → (+/-)-cis-1,1-Dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2acetate

HRID 1198358

Reaktionsgleichung

[C:1]([CH2:3][C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]([OH:18])=[O:17])[CH2:5]1)#[N:2].[C:19](O)([CH3:22])([CH3:21])[CH3:20].C1(N=C=NC2CCCCC2)CCCCC1.C(OCC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([CH2:3][C@H:4]1[O:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[O:7][C@@H:6]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:5]1)#[N:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

(±)-cis-4-(cyanomethyl)-1,5-dioxaspiro[5.5]-undecane-2-acetic acid 3.32 g (13.12 mmol), is dissolved in 15 mL of dichloromethane, cooled to 0° C. and 0.1 g of 4-dimethylaminopyridine (DMAP) added, followed by t-butyl alcohol, and followed by 3.25 g of dicyclohexylcarbodiimide (DCC). This solution is stirred and allowed to slowly warm to room temperature over a 16.5-hour period. TLC shows mainly product, and some slightly lower Rf by-product. The mixture is stirred one hour and 50 mL of dichloromethane is added and stirring continued four hours. One hundred mL of diethyl ether is added and then filtered. The filtrate is concentrated at reduced pressure. This crude concentrate is chromatographed on silica gel and eluted with 4:1 hexane:ethyl acetate to yield (±)-cis-1,1-dimethylethyl 4-(cyanomethyl)-1,5-dioxaspiro[5.5]undecane-2-acetate.

Aufarbeitung

temperatureto slowly warm to room temperature over a 16.5-hour period
stirringThe mixture is stirred one hour
stirringstirring continued four hours
filtrationfiltered
concentrationThe filtrate is concentrated at reduced pressure
concentrationThis crude concentrate
customis chromatographed on silica gel
washeluted with 4:1 hexane

Quellen und Nachweise

ORD-Eintrag: ord-071e3c2ce6eb48d68e849cad5589b338
Quelldatensatz: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05280126

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