Toluene → (S)-3-(Hydroxymethyl)-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

A solution of diisobutylaluminum hydride (DIBAL) in toluene (1 M, 2.2 mL, 2.2 mmol) was added dropwise to a solution of methyl (6S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylate (described in Intermediate 5) (0.184 g, 0.62 mmols) in anhydrous THF at 0° C. The resulting mixture was stirred for 1 h at 0° C., then gradually warmed to ambient temperature and stirred for an additional 1 h. Excess DIBAL was quenched with ice and the mixture was partitioned between water and EtOAc (4×20 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with 5% MeOH in chloroform, to afford the title compound. MS: m/z=268.0 (M+1).

1. temperaturegradually warmed to ambient temperature
2. stirringstirred for an additional 1 h
3. customExcess DIBAL was quenched with ice
4. customthe mixture was partitioned between water and EtOAc (4×20 mL)
5. washThe combined organic layers were washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue was purified by flash column chromatography on silica gel
9. washeluting with 5% MeOH in chloroform

ORD-Eintrag

ord-9683e932af4a4905b4ff9993a98ddb2a

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09227972B2