Isopropanol → (S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxide

HRID 571177Notes

Reaction equation

HRID 571177 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:21])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[OH:10].CCCCCC.C([OH:31])(C)C.CO.C(Cl)(Cl)Cl>C(OCC)(=O)C>[Cl:21][C:6]1[CH:5]=[N+:4]([O-:31])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[OH:10]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 8058HexaneHCID 21584188Chloroform methanolHCID 71092454(S)-2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxyphenyl)ethanol

Product 1

HCID 71092494(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxideYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(S)-2-(3,5-dichloropyridin-4-yl)-1-(3,4-dimethoxyphenyl)ethanol (4 g, 12 mmol) was dissolved in ethyl acetate, and m-CPB acid was added to the solution. The mixture was stirred at RT for 5 hours. The formed solid was collected by filtration, washed with ethyl acetate and dried under vacuum to give 1.72 g of (−) (41% yield). Chiral HPLC analysis Rt=22.16 min; eluent:hexane:isopropanol=6:4; [α]D20=+68.91 (c=0.253, Methanol/CHCl3 1:1); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.15 (s, 2H), 6.99 (m, 1H), 6.79-6.88 (m, 2H), 5.03 (dd, J=8.50, 5.32 Hz, 1H), 3.75-3.98 (m, 6H), 3.42 (dd, J=13.57, 8.56 Hz, 1H), 3.19 (dd, J=13.51, 5.32 Hz, 1H), 2.06-2.15 (m, 1H); MS/ESI+ [MH]+: 344.19

Workup

  1. additionm-CPB acid was added to the solution
  2. filtrationThe formed solid was collected by filtration
  3. washwashed with ethyl acetate
  4. customdried under vacuum
  5. customto give 1.72 g of (−) (41% yield)

Sources & evidence

ORD record
ord-2ff45cfd637141cd8ce590e4268d6426
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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