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Hydrochloric Acid → tert-Butyl 4-(1-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate

HRID 2088887
Notes
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Reaction equation

HRID 2088887 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:12]=[C:11]1[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.O1CCCC1.Cl>C(OCC)(=O)C>[OH:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13]([CH:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[N:12]=[C:11]1[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 67954713tert-Butyl 4-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 67113226tert-Butyl 4-(1-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylateYield 79.5%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

Combine tert-butyl 4-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-2-yl)piperidine-1-carboxylate (6.88 g, 14.84 mmol), tetrahydrofuran (136 mL) and 1 N aqueous hydrochloric acid (25 mL). Stir the reaction at room temperature overnight. Dilute with ethyl acetate and wash with saturated aqueous sodium chloride and saturated aqueous sodium bicarbonate. Extract the combined aqueous layers with 9:1 dichloromethane:isopropyl alcohol. Dry the combined organic layers over anhydrous sodium sulfate, filter, and concentrate in vacuo. Purify by silica gel chromatography, eluting with hexanes to 50% ethyl acetate in hexanes to ethyl acetate to 10% methanol in ethyl acetate to 10% methanol in dichloromethane, to give the title compound as a white solid (4.48 g, 79%). MS (ES) m/z=380 [M]+.

Workup

  1. customthe reaction at room temperature overnight
  2. washwash with saturated aqueous sodium chloride and saturated aqueous sodium bicarbonate
  3. extractionExtract the combined aqueous layers with 9:1 dichloromethane
  4. dry with materialDry the combined organic layers over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by silica gel chromatography
  8. washeluting with hexanes to 50% ethyl acetate in hexanes to ethyl acetate to 10% methanol in ethyl acetate to 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-578bde80f9ee481ebbaec8fba76df9e3
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436002B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes