Pyridine → 3-Hydroxy-hexahydro-pyrrolo[3,2-b]pyrrole-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

Temperatur

0 °C

A solution containing 10 (868 mg, 1.8 mmol) in THF (10 mL) was cooled to 0° C. HF.pyridine reagent (1 mL, 36 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 16 h, the reaction mixture was diluted with EtOAc and washed successively with water, aqueous NaHCO3, water, and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc) to afford 600 mg (90%) of 11. 1H NMR (CDCl3, 300 MHz): δ7.29 (m, 5H), 5.10 (app dd, J=22.7, 12.5 Hz, 2H), 4.32 (m, 4H), 3.71 (m, 2H), 3.58 (m, 1H), 3.38 (m, 1H), 3.17 (m, 1H), 2.14 (m, 1H), 2.02 (m, 1H), 1.42 (s, 9H) ppm. Mass spectrum, m/z [363.2] (M+H)+.

1. temperatureto warm to ambient temperature
2. washwashed successively with water, aqueous NaHCO3, water, and brine
3. dry with materialdried over anhydrous Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude product was purified by flash silica gel chromatography (1:1 hexanes/EtOAc)

ORD-Eintrag

ord-b7088a35d8b54d3b8c5f6da471b268e8

Quelldatensatz

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08415486B2