Dimethylformamide → HCID 178501093, compound

HRID 2283495Notes

Reaction equation

HRID 2283495 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C@H:11]2[CH2:16][CH2:15][C@H:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]2)[CH2:9]O)=[N:6][CH:7]=1.[H-].[Na+].CI.CN([CH:28]=[O:29])C>O.C(OCC)(=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C@H:11]2[CH2:12][CH2:13][C@H:14]([C:17]([O:19][CH3:20])=[O:18])[CH2:15][CH2:16]2)([O:29][CH3:28])[CH3:9])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178501090HCID 178501090, compound

Product 1

HCID 178501093HCID 178501093, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Racemic methyl trans-4-[1-(5-bromopyridin-2-yl)hydroxyethyl]cyclohexanecarboxylate (500 mg, 1.461 mmol) was dissolved in DMF (7.3 mL) and cooled to 0° C. Sodium hydride (60 wt %, 117 mg, 2.92 mmol) was added in one portion. The mixture was stirred and allowed to warm to room temperature. After 20 minutes, methyl iodide (0.183 mL, 2.92 mmol) was added, and the reaction was stirred at room temperature for 30 minutes. The mixture was diluted with water, ethyl acetate, and brine. The layers were separated, and the organic portion dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel column chromatography (20% EtOAc:hexanes) gave racemic methyl trans-4-[1-(5-bromopyridin-2-yl)-1-methoxyethyl]cyclohexanecarboxylate as a colorless oil. MS ESI calcd. for C16H23BrNO3 [M+H]+ 356 and 358. found 356 and 358. 1H NMR (500 MHz, DMSO-d6) 8.64 (d, J=2.2 Hz, 1H), 8.01 (dd, J=2.3, 8.5 Hz, 1H), 7.37 (d, J=9.1 Hz, 1H), 3.54 (s, 3H), 2.98 (s, 3H), 2.20-1.50 (m, 5H), 1.55 (s, 3H), 1.40-0.75 (m, 5H).

Workup

  1. temperatureto warm to room temperature
  2. stirringthe reaction was stirred at room temperature for 30 minutes
  3. customThe layers were separated
  4. dry with materialthe organic portion dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification via silica gel column chromatography (20% EtOAc:hexanes)

Sources & evidence

ORD record
ord-4550e5572c1f4a52a881546c69445f6f
Source dataset
uspto-grants-2015_09
Patent number
US09145391B2

Reaction notes

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