Triethylamine → HCID 11200112, compound

HRID 1391506Notes

Reaction equation

HRID 1391506 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(N(CC)CC)C.C(OCC)(=O)C>ClCCl.CN(C1C=CC=CN=1)C>[Si:21]([O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 59674890HCID 59674890, compound

Product 1

HCID 11200112HCID 11200112, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

The tert-butyl 4-(3-hydroxyphenyl)-3,6-dihydropyridine-1(2H)-carboxylate (4.01 g, 14.58 mmol), tert-butyldimethylsilyl chloride (2.73 g, 18.22 mmol), triethylamine (4.01 g, 40.0 mmol) and a catalytic amount of dimethylaminopyridine (100 mg, 0.80 mmol) were mixed in dichloromethane (100 mL) at room temperature for 16 h. The solvent was removed at reduced pressure and the resulting semisolid dissolved in diethylether (100 mL). The solution was extracted with 1N aqueous hydrochloric acid (2×50 mL), extracted with saturated aqueous sodium bicarbonate (2×50 mL), and extracted with saturated with saturated aqueous ammonium chloride (2×50 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The tert-butyl 4-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3,6-dihydropyridine-1(2H)-carboxylate (4.8 g, 12.33 mmol) was isolated as a clear colorless oil by preparative silica chromatography (5% ethyl acetate/95% hexanes). HRMS m/z 388.2305 (calcd for M−H 388.2302.)

Workup

  1. customThe solvent was removed at reduced pressure
  2. dissolutionthe resulting semisolid dissolved in diethylether (100 mL)
  3. extractionThe solution was extracted with 1N aqueous hydrochloric acid (2×50 mL)
  4. extractionextracted with saturated aqueous sodium bicarbonate (2×50 mL)
  5. extractionextracted with saturated with saturated aqueous ammonium chloride (2×50 mL)
  6. dry with materialThe solution was dried over sodium sulfate and solvent
  7. customremoved at reduced pressure

Sources & evidence

ORD record
ord-d6491283df9e4fb1822cd392787e70c0
Source dataset
uspto-grants-2008_03
Patent number
US07338965B2

Reaction notes

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