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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 222168Erstellt: 25. Oktober 2026

Acetic Acid → (1R,2S,3R,5S)-3-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol

https://huagongshe.com/reaction/222168

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktAcetic AcidHCID 176—
EduktWaterHCID 962—
Edukt1-Aminoindane, (S)-HCID 7000084—
Edukt(4aS,6R,7R,7aR)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)-7-methylhexahydrocyclopenta[d]-[1,3]dioxin-7-olHCID 66618631—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt(1R,2S,3R,5S)-3-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)cyclopentane-1,2-diolHCID 6661809176%

Reaktionsschritte

To a solution of (4aS,6R,7R,7aR)-6-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2-(4-methoxyphenyl)-7-methylhexahydrocyclopenta[d]-[1,3]dioxin-7-ol (312 mg, 0.594 mmol, as prepared following the procedure in Example 1a-d, using (S)-(+)-1-aminoindan in step c) in THF (1.17 mL) and water (1.17 mL) was added AcOH (3.51 mL, 61.7 mmol) under an atmosphere of nitrogen. The mixture was stirred at rt overnight. The solvent was removed in vacuo and the residue was purified by silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to afford the title compound as a white solid (182 mg, 76%). LC/MS: Rt=0.85 min, ES+ 381 (FA standard).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08207177B2
Quelldatensatzuspto-grants-2012_06
ORD IDord-2ae5f79e0a084b2888bc16d1c21d0be2
Quellennotizuspto-grants-2012_06