Methanol → (9H-fluoren-9-yl)methyl piperidine-1-carboxylate

HRID 1865793Notizen

Reaktionsgleichung

C1C=CC(C(Cl)(C2C(Cl)=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:22]([N:39]([CH2:47]COCCO)[CH2:40][C:41]1C=CC=[CH:43][CH:42]=1)([O:24][CH2:25][CH:26]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]2[C:27]1=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:23].N1C=CC=CC=1.CO>C1COCC1>[C:22]([N:39]1[CH2:40][CH2:41][CH2:42][CH2:43][CH2:47]1)([O:24][CH2:25][CH:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[C:38]1=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:23]

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

THF (15 ml) was added to 2-Chlorotrityl chloride resin (4.0 g, 1.2 mmol/g) and the mixture was agitated for 25 min. FmocN(Bn)CH2CH2OCH2CH2OH (6.1 g, 14.7 mmol) in THF (25 ml) was added followed by pyridine (850 μl, 10.5 mmol) and the mixture was heated to 65° C. for 15 h. MeOH (5 ml) was added and heating was continued for 35 min. The resin was filtered, washed with DMF (3×), CH2Cl2 (3×). MeOH (3×) and Et2O (3×) to give 5.0 g. A small sample was dried carefully and deprotected with DCM/piperidine (1:1) for 30 min. Photometric determination of the resulting Fmoc-piperidine adduct (absorption at 301 nm) gave a resin loading of 0.45 mmol/g.

Aufarbeitung

temperatureheating
waitwas continued for 35 min
filtrationThe resin was filtered
washwashed with DMF (3×), CH2Cl2 (3×)
customMeOH (3×) and Et2O (3×) to give 5.0 g
customA small sample was dried carefully
waitdeprotected with DCM/piperidine (1:1) for 30 min

Quellen und Nachweise

ORD-Eintrag: ord-76012879e8d54af9b559a7f94df9ab73
Quelldatensatz: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07629318B2

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