Dimethylformamide → HCID 68287222, compound

HRID 587136Notes

Reaction equation

HRID 587136 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1O)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].I[CH3:18].CN([CH:22]=[O:23])C>>[C:3]([N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]1[CH2:18][O:23][CH3:22])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 29926342HCID 29926342, compound

Product 1

HCID 68287222HCID 68287222, compoundYield 85%

Procedure

A suspension of sodium hydride (0.13 g, 5.4 mmol) in DMF (4 mL) was cooled with ice and a solution of the intermediate alcohol of Step 2 (0.97 g, 4.5 mmol) in DMF (1 mL) was added dropwise. After stirring for 30 min at room temperature iodomethane (0.96 g, 6.8 mmol) was added and the mixture was stirred over night. The mixture was quenched with saturated NH4Cl-solution and extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated under reduced pressure to leave the crude (R)—N-Boc-2-methoxymethylpiperidine (0.88 g, 85%).

Workup

  1. temperaturewas cooled with ice
  2. additionwas added
  3. customThe mixture was quenched with saturated NH4Cl-solution
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1167c80560fc47b39bbb61dcfed5dcf3
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Reaction notes

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