Methanol → n-(3-Hydroxymethylphenyl)-n-(ethylsulfonyl)pyrid-3-ylmethylamine

Temperature

0 °C

Into a −78° C. solution of N-(3-methoxycarbonylphenyl)-N-(ethanesulfonyl)pyrid-3-ylmethylamine (75 g, 0.224 mole, 1 eq) in THF was added slowly DIBAl-H (561 mL, 1M in toluene, 2.5 eq). The mixture was stirred for 1 hour and then was warmed to 0° C. with an ice water bath and stirred for 2 h. The reaction was carefully quenched with methanol (18.50 mL, 0.396 mole, 1.8 eq). It was then diluted with ether (4650 mL) and Saturated Rochelle's salt (2775 mL) and stirred vigorously overnight. The layers were separated and the aqueous extracted with EtOAc (2000 mL). The combined organics were washed with brine, dried with MgSO4, filtered and concentrated. The residue was chromatographed, eluting with 1:1 DCM/EtOAc to give the title compound as a white solid (51.4 g, 43% Yield).

1. stirringstirred for 2 h
2. stirringstirred vigorously overnight
3. customThe layers were separated
4. extractionthe aqueous extracted with EtOAc (2000 mL)
5. washThe combined organics were washed with brine
6. dry with materialdried with MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was chromatographed
10. washeluting with 1:1 DCM/EtOAc

ORD record

ord-3c5d2e4dd90a4133b43343b0bd2ae7d8

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06800651B2