Diisobutylaluminum hydride → [3-Phenyl-1-(toluene-4-sulfonyl)-1H-indol-2-yl]methanol

To a stirred solution of 3-phenyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (3.24 g, 7.72 mmol) in toluene (40 mL) at −78° C. and under a nitrogen atmosphere was added 1.0M DIBAL-H in toluene (23.2 mL, 23.2 mmol). The reaction mixture was stirred at −78° C. for 15 min then at −10° C. for 30 min. After re-cooling to −78° C., the reaction mixture was quenched with water (20 mL) then allowed to warm to RT. The mixture was partitioned between EtOAc and 1.0M HCl and the aqueous phase was extracted with additional EtOAc (×3). The combined organic fractions were washed with water, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in pentane) affording the title compound as a white foam (2.49 g, 85%). LCMS (Method C): RT 4.77 min [M+Na]+ 400.1

1. waitat −10° C. for 30 min
2. temperatureAfter re-cooling to −78° C.
3. customthe reaction mixture was quenched with water (20 mL)
4. temperatureto warm to RT
5. customThe mixture was partitioned between EtOAc and 1.0M HCl
6. extractionthe aqueous phase was extracted with additional EtOAc (×3)
7. washThe combined organic fractions were washed with water
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated in vacuo
10. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in pentane)

ORD record

ord-ea44d798d2ae4933b79b4d8b395a5f18

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2