Imidazole → HCID 131734949, compound

HRID 921907Notes

Reaction equation

HRID 921907 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].[Cl-].[NH4+]>CN(C=O)C.CCOCC>[Si:21]([O:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate

Product 1

HCID 131734949HCID 131734949, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a round bottom flask charged with (+/−)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (2 g, 9.21 mmol) in DMF (2 mL) was added imidazole and TBS-Cl (1.387 g, 9.21 mmol). The reaction mixture was stirred at room temperature 2 d. The reaction mixture was poured into a separatory funnel containing half-saturated aqueous ammonium chloride and ether. The aqueous layer was extracted with ether (2×). The combined organics were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. (+/−)-tert-Butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)morpholine-4-carboxylate (3.039 g) was isolated as a white pasty solid.

Workup

  1. additionThe reaction mixture was poured into a separatory funnel
  2. extractionThe aqueous layer was extracted with ether (2×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5e4cc2a0e8e4cdb88a7d81752fb4c5a
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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