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

HRID 392428Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:6]=[C:7]([N:11]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)=O.CC(C[AlH]CC(C)C)C.CO>C1COCC1.CCOCC.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]([N:11]([CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-3c5d2e4dd90a4133b43343b0bd2ae7d8
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800651B2

Reaction notes

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