2,6-Dichloropyridine → HCID 57893630, compound

HRID 1822002Notes

Reaction equation

HRID 1822002 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C@H:13]([OH:16])[CH2:12][C@@H:11]1[CH3:17])=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](Cl)[N:20]=1>CS(C)=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C@H:13]([O:16][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([Cl:18])[N:20]=2)[CH2:12][C@@H:11]1[CH3:17])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 450974401-Piperidinecarboxylicacid,4-hydroxy-2-methyl-,1,1-dimethylethylester,(2S,4S)-(9CI)

Product 1

HCID 57893630HCID 57893630, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

Add sodium hydride (95%, 0.318 g) to a solution of 4-hydroxy-cis-2-methyl-piperidine-1-carboxylic acid tert-butyl ester isomer 2 (preparation 3, 2.465 g) in DMSO (100 mL) and heat in an oil bath at 65° C. After 30 min., add 2,6-dichloropyridine (1.864 g) and beat at 100° C. After 4 hr., partition between ethyl acetate-hexane (1:4) and saturated aqueous NaCl aqueous NaCl, dry over anhydrous sodium sulfate, evaporate and purify on a 35 g silica gel column eluting with ethyl acetate-hexane (1:39) to give the title compound (3.26 g). 1H NMR (CDCl3): 7.50 (t, 1H), 6.87 (d, 1H), 6.61 (d, 1H), 5.38 (m, 1H), 4.35 (m, 1H), 3.89 (m, 1H), 3.22 (m, 1H), 1.93 (m, 3H), 1.75 (m, 1H), 1.46 (s, 9H), 1.26 (d, 3H).

Workup

  1. custombeat at 100° C
  2. waitAfter 4 hr
  3. custom, partition between ethyl acetate-hexane (1:4) and saturated aqueous NaCl aqueous NaCl
  4. dry with materialdry over anhydrous sodium sulfate
  5. customevaporate
  6. custompurify on a 35 g silica gel column
  7. washeluting with ethyl acetate-hexane (1:39)

Sources & evidence

ORD record
ord-d15c16a245cf4aedb10224fbf3bed718
Source dataset
uspto-grants-2009_10
Patent number
US07608629B2

Reaction notes

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